2-Benzyloxycarbonylamino-3-(tetrahydrofuran-2-yloxy)propionic acid → (4S)-1-[(2S,3S)-3-{N2-[2(S)-Benzyloxycarbonylamino-3-(tetrahydrofuran-2-yloxy)propanoyl]-L-asparaginyl}amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide

HRID 1780269Notes

Reaction equation

HRID 1780269 reaction equation
C(OC([NH:8][C@H:9]([C:14]([NH:16][C@@H:17]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:18]([OH:34])[C:19]([N:21]1[CH2:32][C@@H:31]([Cl:33])[CH2:30][C@H:22]1[C:23]([NH:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])=[O:15])[CH2:10][C:11](=[O:13])[NH2:12])=O)(C)(C)C.[CH2:42]([O:49][C:50]([NH:52][CH:53]([CH2:57][O:58][CH:59]1[CH2:63][CH2:62][CH2:61][O:60]1)[C:54]([OH:56])=O)=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH2:42]([O:49][C:50]([NH:52][C@@H:53]([CH2:57][O:58][CH:59]1[CH2:63][CH2:62][CH2:61][O:60]1)[C:54]([NH:8][C@H:9]([C:14]([NH:16][C@@H:17]([CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C@H:18]([OH:34])[C:19]([N:21]1[CH2:32][C@@H:31]([Cl:33])[CH2:30][C@H:22]1[C:23]([NH:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])=[O:15])[CH2:10][C:11](=[O:13])[NH2:12])=[O:56])=[O:51])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

3

Reactant 2

HCID 190499152-Benzyloxycarbonylamino-3-(tetrahydrofuran-2-yloxy)propionic acidHCID 70048547(4S)-1-[(2S,3S)-3-(N2-t-Butoxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide

Product 1

HCID 86750835(4S)-1-[(2S,3S)-3-{N2-[2(S)-Benzyloxycarbonylamino-3-(tetrahydrofuran-2-yloxy)propanoyl]-L-asparaginyl}amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide

Procedure

Following a procedure similar to that described in Example 16, but using 100 mg (0.26 mmol) of (4S)-1-[2S,3S)-3-(N2 -t-butoxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide (prepared as described in Example 65) and 2-benzyloxycarbonylamino-3-(tetrahydrofuran-2-yloxy)propionic acid, 83 mg of the title compound were obtained as a colorless powder, melting at 64°-71° C.

Sources & evidence

ORD record
ord-0da1f032716a4738976aef7a17f7c7ed
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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