Hydrogen chloride-ethyl acetate → 4-[(3s,4s)-3-({[(1r)-1-(1-Naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-4-oxobutanoic acid hydrochloride

HRID 732675Notes

Reaction equation

HRID 732675 reaction equation
C(OC([N:8]([CH2:21][C@@H:22]1[C@@H:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][N:24]([C:33](=[O:39])[CH2:34][CH2:35][C:36]([OH:38])=[O:37])[CH2:23]1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.[ClH:40].C(OCC)(=O)C>>[ClH:40].[C:11]1([C@H:9]([NH:8][CH2:21][C@@H:22]2[C@@H:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][N:24]([C:33](=[O:39])[CH2:34][CH2:35][C:36]([OH:38])=[O:37])[CH2:23]2)[CH3:10])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 689124824-[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-4-oxobutanoic acid

Product 1

HCID 689139704-[(3s,4s)-3-({[(1r)-1-(1-Naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-4-oxobutanoic acid hydrochloride

Procedure

The thus obtained 4-[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-4-oxobutanoic acid was subjected to Boc-elimination with 4 M hydrogen chloride/ethyl acetate to obtain 4-[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-4-oxobutanoic acid hydrochloride.

Sources & evidence

ORD record
ord-861089095a6c46eaad07f384fa4261d8
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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