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1212257-18-5

1212257-18-5 Structure

1212257-18-5 Structure
IdentificationBack Directory
[Name]

FMOC-L-CYCLOPROPYLGLYCINE
[CAS]

1212257-18-5
[Synonyms]

FMOC-L-CYCLOPROPYLGLYCINE
(S)-Fmoc-cyclopropylglycine
N-Fmoc-S-2-Cyclopropylglycine
Fmoc-(S)-2-cyclopropylglycine
Fmoc-(S)-Amino-cyclopropyl-acetic acid
Fmoc-L-cyclopropylglycine≥ 99% (HPLC, Chiral purity)
N-α-(9-Fluorenylmethoxycarbonyl)-L-α-cyclopropylglycine
(9H-Fluoren-9-yl)MethOxy]Carbonyl Cyclopropylglycine (EE >98%)
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid
(2S)-2-cyclopropyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetic acid
Cyclopropaneacetic acid, α-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (αS)-
(alphaS)-alpha-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]cyclopropaneacetic acid
L-2-Cyclopropylglycine, N-FMOC protected, (S)-Cyclopropyl({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetic acid
[Molecular Formula]

C20H19NO4
[MDL Number]

MFCD06659145
[MOL File]

1212257-18-5.mol
[Molecular Weight]

337.37
Chemical PropertiesBack Directory
[Boiling point ]

577.1±33.0 °C(Predicted)
[density ]

1.332±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[form ]

powder
[pka]

3.85±0.10(Predicted)
[color ]

White
[Optical Rotation]

17.134°(C=0.01g/ml DCM)
[InChI]

InChI=1S/C20H19NO4/c22-19(23)18(12-9-10-12)21-20(24)25-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18H,9-11H2,(H,21,24)(H,22,23)/t18-/m0/s1
[InChIKey]

YMLZBPTXRMNAFP-SFHVURJKSA-N
[SMILES]

C1(COC(=O)N[C@H](C(O)=O)C2CC2)C2C=CC=CC=2C2C=CC=CC=21
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H335-H315-H319
[Precautionary statements ]

P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
[Hazard Codes ]

Xi
[HS Code ]

2922498590
Hazard InformationBack Directory
[Chemical Properties]

White powder
[Uses]

Fmoc-L-cyclopropylglycine is used in preparation of tailored Cyclodepsipeptides as potent non-covalent serine protease inhibitors.
[Synthesis]

9-Fluorenylmethyl chloroformate

28920-43-6

L-Cyclopropylglycine

49606-99-7

FMOC-L-CYCLOPROPYLGLYCINE

1212257-18-5

GENERAL STEPS: 2.3 g of Na2CO3 was dissolved in 34 mL of water and chloroformic acid-9-fluorenylmethyl ester and (S)-2-amino-2-cyclopropylacetic acid were added with stirring. The reaction mixture was stirred at room temperature. After completion of the reaction, the product was characterized by FT-IR and NMR.FT-IR (pure): 2669, 2335, 2159, 2106, 1785, 1689, 1550, 1489, 1463, 1433, 1369, 1296, 1253, 1172, 1128, 1001 cm^-1.^1H NMR ( CDCl3, 600 MHz): δ = 7.76 (d, 2H, J = 7.2 Hz), 7.60-7.59 (m, 2H), 7.41-7.39 (m, 2H), 7.32-7.30 (m, 2H), 5.36 (d, 1H, J = 6 Hz), 4.45-4.39 (m, 2H), 4.24-4.21 (m, 1H ), 3.83-3.81 (m, 1H), 1.14-1.13 (m, 1H), 0.65-0.46 (m, 5H) ppm. ^13C NMR (CDCl3, 150 MHz): δ = 176.6, 156.2, 143.9, 143.8, 141.4, 127.9, 127.2, 125.2, 125.1 , 120.1, 67.3, 57.4, 47.3, 13.9, 3.4 ppm. HRMS (ESI): m/z [M + Na]^+ Calculated value C20H19NO4Na 360.1206, measured value 360.1193.

[References]

[1] Journal of the American Chemical Society, 2016, vol. 138, # 5, p. 1698 - 1708
[2] Patent: WO2016/138288, 2016, A1. Location in patent: Page/Page column 124
Spectrum DetailBack Directory
[Spectrum Detail]

FMOC-L-CYCLOPROPYLGLYCINE(1212257-18-5)1HNMR
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478183-62-9 214750-76-2 220497-61-0 1332765-55-5 923012-40-2 49606-99-7