| Identification | More | [Name]
Fmoc-L-hydroxyproline | [CAS]
88050-17-3 | [Synonyms]
(2S,4R)-N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
(2S,4R)-N-ALPHA-(Y-FLUORENYLMETHOXYCARBONYL)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
FMOC-(2S,4R)-(-)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
FMOC-HYDROXYPROLINE
FMOC-HYP-OH
FMOC-HYP-OH (TRANS)
FMOC-L-4-HYDROXYPROLINE
FMOC-L-HYDROXYPROLINE
FMOC-L-HYP-OH
FMOC-L-T-4-HYDROXYPROLINE
FMOC-L-TRANS-4-HYDROXYPROLINE
FMOC-TRANS-4-HYDROXY-L-PROLINE
FMOC-TRANS-4-HYP-OH
N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-TRANS-L-HYDROXYPROLINE
N-ALPHA-FMOC-L-TRANS-4-HYDROXYPROLINE
N-FMOC-L-TRANS-4-HYDROXYPROLINE
N-FMOC-TRANS-4-HYDROXY-L-PROLINE
RARECHEM EM WB 0137
N-Fmoc-cis-4-hydroxy-D-proline
FMOC-HYP-OH 99%MIN | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C20H19NO5 | [MDL Number]
MFCD00151929 | [Molecular Weight]
353.37 | [MOL File]
88050-17-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
189-193 °C
| [Boiling point ]
595.5±50.0 °C(Predicted) | [density ]
1.407±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
3.74±0.40(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]20/D 60±2°, c = 1% in methanol | [Detection Methods]
HPLC,NMR | [BRN ]
4574378 | [InChI]
InChI=1S/C20H19NO5/c22-12-9-18(19(23)24)21(10-12)20(25)26-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18,22H,9-11H2,(H,23,24)/t12-,18+/m1/s1 | [InChIKey]
GOUUPUICWUFXPM-XIKOKIGWSA-N | [SMILES]
N1(C(OCC2C3=C(C=CC=C3)C3=C2C=CC=C3)=O)C[C@H](O)C[C@H]1C(O)=O | [CAS DataBase Reference]
88050-17-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Light brown solid | [Uses]
peptide synthesis | [reaction suitability]
reaction type: Fmoc solid-phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of Fmoc-L-hydroxyproline from methyl 9-fluorenyl chloroformate and L-hydroxyproline is as follows:
Example 2: Synthesis of (2S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid
1. Sodium bicarbonate (80 g) and water (400 ml) were added to a solution of tetrahydrofuran (THF, 200 ml) containing (2S,4R)-4-hydroxy-L-proline (100 g) at 25-30 °C.
2. A solution of 9-fluorenylmethoxycarbonyl (Fmoc) chloride (226 g) dissolved in 200 ml of THF was added slowly.
3. The reaction mixture was stirred continuously at 25-30°C for 10-12 hours until the reaction was complete.
4. Upon completion of the reaction, the reaction was terminated by the addition of an appropriate amount of water.
5. The reaction mixture was washed with diisopropyl ether (DIPE) and subsequently acidified with 1N hydrochloric acid.
6. The acidified mixture was continued to be stirred for 2-3 hours to promote precipitation of the product.
7. The solid product was collected by filtration to give 150 g of Fmoc-L-hydroxyproline as a white solid.
Product Characterization:
1H NMR (300 MHz, DMSO-d6): δ 1.89-2.24 (m, 2H), 3.34-3.43 (m, 2H), 3.43-3.54 (m, 0.5H), 4.12-4.21 (m, 3H), 4.25 (s, 2H), 4.28-4.42 (m, 0.5H), 5.16 (brs, 1H) , 7.29-7.34 (m, 2H), 7.38-7.65 (m, 2H), 7.63-7.65 (m, 2H).
Melting point: 188-190°C.
Mass spectrum (M + H): 354.33. | [References]
[1] Tetrahedron Letters, 1994, vol. 35, # 51, p. 9509 - 9512
[2] Angewandte Chemie - International Edition, 2009, vol. 48, # 10, p. 1784 - 1787
[3] Patent: US9518048, 2016, B2. Location in patent: Page/Page column 24 |
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