HCID 13848990, compound → HCID 13849017, compound

HRID 649515Notes

Reaction equation

HRID 649515 reaction equation
CC(C)(OC([NH:7][C@@H:8]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9](=[O:30])[CH2:10][N:11]([CH3:29])[C:12]([N:14]1[CH2:28][CH2:27][CH2:26][C@H:15]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:13])=O)C.Cl.C(OCC)(=O)C>>[NH2:7][C@@H:8]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9](=[O:30])[CH2:10][N:11]([CH3:29])[C:12]([N:14]1[CH2:28][CH2:27][CH2:26][C@H:15]1[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])=[O:13]

Participants

3

Reactant 2

HCID 13848990HCID 13848990, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 13849017HCID 13849017, compoundYield 97.7%

Procedure

A solution of 1-[[[(S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester (7.12 g., 13.6 mmole) is stirred in a saturated solution of hydrochloric acid/ethyl acetate for one hour. The resulting precipitate is collected and washed with ethyl acetate to give 5.63 g of 1-[[[(S)-3-amino-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester; m.p. 174°-175°; [α]D25 =+16.20°. TLC (silica gel; chloroform:methanol:acetic acid, 4:1:1) Rf =0.60.

Workup

  1. customThe resulting precipitate is collected
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ae71df3c7c154c2e82585a7a45cc57d9
Source dataset
uspto-grants-1988_04
Patent number
US04740508

Reaction notes

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