7-Methoxy-1-benzofuran-2-carboxylic acid → AHPBA 44a

HRID 1780264Notes

Reaction equation

HRID 1780264 reaction equation
C(O[C:6]([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:7])(C)(C)C.[CH3:42][O:43][C:44]1[C:52]2[O:51][C:50](C(O)=O)=[CH:49][C:48]=2[CH:47]=[CH:46][CH:45]=1>>[CH3:42][O:43][C:44]1[C:52]2[O:51][C:50]([C:6]([NH:8][C@H:9]([C:14]([NH:16][C@@H:17]([CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C@H:18]([OH:34])[C:19]([N:21]3[CH2:32][C@@H:31]([Cl:33])[CH2:30][C@H:22]3[C:23]([NH:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])=[O:20])=[O:15])[CH2:10][C:11](=[O:13])[NH2:12])=[O:7])=[CH:49][C:48]=2[CH:47]=[CH:46][CH:45]=1

Participants

3

Reactant 2

HCID 6060377-Methoxy-1-benzofuran-2-carboxylic 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 473108AHPBA 44aYield 65.4%

Procedure

Following a procedure similar to that described in Example 16, but using 155 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 50 mg (0.26 mmol) of 7-methoxy-2-benzofurancarboxylic acid, 114 mg of the title compound were obtained as a colorless powder, melting at 125°-136° C.

Sources & evidence

ORD record
ord-0ea7d6bd40324e83a9b571e28c5c0da9
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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