Methanol → 3-[[(S)-2-amino-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester, hydrochloride
Reaction equation
CC(C)(OC([NH:7][C@@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:10])=O)C.C(Cl)(Cl)[Cl:33].CO>Cl.C(O)(=O)C>[ClH:33].[NH2:7][C@@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])=[O:10]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of the phenylmethyl ester product from part (a) (13.65 g., 32 mmole) in 1.5N hydrogen chloride gas in acetic acid solution (90 ml.) is stirred for 90 minutes at room temperature, and then the solvent is evaporated in vacuo. The residue is triturated in ether and the resulting white precipitate is collected to give 11.45 g. of crude product as a powdery white solid; m.p. 169°-175°. TLC (silica gel; chloroform:methanol:acetic acid, 6:1:1) Rf =0.52. One recrystallization from acetonitrile gives an analytical sample of 3-[[(S)-2-amino-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester, hydrochloride as white needles; m.p. 170.5°-175°.
Workup
- customthe solvent is evaporated in vacuo
- customThe residue is triturated in ether
- customthe resulting white precipitate is collected
- customto give 11.45 g
- customOne recrystallization from acetonitrile
Sources & evidence
- ORD record
- ord-7aaa0c2d2a1b42e9971aabc10cd0525b
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04963539
Reaction notes
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