| Identification | Back Directory | [Name]
Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, (2S)- | [CAS]
52558-24-4 | [Synonyms]
Boc-(S)-isoserine
N-tert-Butyloxycarbonyl-(S)-isoserine
(S)-3-(Boc-aMino)-2-hydroxy-propanoic acid
3-tert-ButoxycarbonylaMino-(S)-2-hydroxy-propionic acid
(S)-3-(tert-Butyloxycarbonylamino)-2-hydroxypropionic acid
(S)-3-((tert-Butoxycarbonyl)aMino)-2-hydroxypropanoic acid
(2S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-hydroxy-propanoic acid
(2S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, (2S)- | [Molecular Formula]
C8H15NO5 | [MDL Number]
MFCD17011798 | [MOL File]
52558-24-4.mol | [Molecular Weight]
205.21 |
| Chemical Properties | Back Directory | [Boiling point ]
391.7±32.0 °C(Predicted) | [density ]
1.240±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [pka]
3.58±0.11(Predicted) | [Appearance]
White to off-white Solid | [Optical Rotation]
Consistent with structure | [InChI]
InChI=1S/C8H15NO5/c1-8(2,3)14-7(13)9-4-5(10)6(11)12/h5,10H,4H2,1-3H3,(H,9,13)(H,11,12)/t5-/m0/s1 | [InChIKey]
JJCAYTVAYSGVLA-YFKPBYRVSA-N | [SMILES]
C(O)(=O)[C@@H](O)CNC(OC(C)(C)C)=O |
| Hazard Information | Back Directory | [Synthesis]
(S)-Isoserine (21 g, 0.20 mol) was dissolved in tetrahydrofuran (100 mL), followed by addition of a solvent mixture of 10% aqueous sodium hydroxide (100 mL) and di-tert-butyl dicarbonate (50 mL, 0.22 mol). The reaction mixture was stirred at room temperature for 9 hours. After completion of the reaction, the aqueous phase was adjusted to pH 2 with 4 mol/L hydrochloric acid and then extracted with dichloromethane/methanol (v/v=5/1, 50 mL x 3). The organic phases were combined and dried with anhydrous sodium sulfate. After drying, the desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give 3-tert-butoxycarbonylamino-(S)-2-hydroxypropionic acid as a colorless oil (35 g, yield: 85%). | [References]
[1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2012, vol. 27, # 2, p. 302 - 310
[2] Journal of Organic Chemistry, 2018, vol. 83, # 9, p. 4973 - 4980
[3] Patent: CN108341752, 2018, A. Location in patent: Paragraph 0507; 0508; 0509; 0510
[4] Patent: WO2010/132757, 2010, A2. Location in patent: Page/Page column 98-99
[5] Patent: WO2011/44503, 2011, A1. Location in patent: Page/Page column 67 |
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