6-Nitroquinoxaline-2-carboxylic acid → (4S)-1-{(2S,3S)-3-[N2-(6-Nitro-2-quinoxalinecarbonyl)-L-asparaginyl]amino-2-hydroxy-4-phenylbutyryl}-4-chloro-N-t-butyl-L-prolinamide

HRID 1780265Notes

Reaction equation

HRID 1780265 reaction equation
Cl.[NH2:2][C@H:3]([C:8]([NH:10][CH:11]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:12]([OH:28])[C:13]([N:15]1[CH2:26][CH:25]([Cl:27])[CH2:24][C@H:16]1[C:17]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:14])=[O:9])[CH2:4][C:5](=[O:7])[NH2:6].[N+:36]([C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[N:45]=[C:44]([C:49](O)=[O:50])[CH:43]=[N:42]2)([O-:38])=[O:37]>>[N+:36]([C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[N:45]=[C:44]([C:49]([NH:2][C@H:3]([C:8]([NH:10][C@@H:11]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C@H:12]([OH:28])[C:13]([N:15]1[CH2:26][C@@H:25]([Cl:27])[CH2:24][C@H:16]1[C:17]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:14])=[O:9])[CH2:4][C:5](=[O:7])[NH2:6])=[O:50])[CH:43]=[N:42]2)([O-:38])=[O:37]

Participants

3

Reactant 2

HCID 190498156-Nitroquinoxaline-2-carboxylic acidHCID 677230331-[3-(L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide hydrochloride

Product 1

HCID 86750833(4S)-1-{(2S,3S)-3-[N2-(6-Nitro-2-quinoxalinecarbonyl)-L-asparaginyl]amino-2-hydroxy-4-phenylbutyryl}-4-chloro-N-t-butyl-L-prolinamideYield 29.6%

Procedure

Following a procedure similar to that described in Example 14, but using 490 mg (0.92 mmol) of 1-[3-(L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide hydrochloride and 220 mg (1.01 mmol) of 6-nitroquinoxaline-2-carboxylic acid (prepared as described in Preparation 22), 190 mg of the title compound were obtained as a pale yellow powder, melting at 153°-156° C.

Sources & evidence

ORD record
ord-ff77e9df036441839247aff78b65bb12
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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