N-Cbz-L-2-amino-4-sulfamoylbutyric acid → (4S)-1-{(2S,3S)-3-[2(S)-Benzyloxycarbonylamino-4-sulfamoylbutyryl]amino-2-hydroxy-4-phenylbutyryl}-4-chloro-N-t-butyl-L-prolinamide

HRID 1780263Notes

Reaction equation

HRID 1780263 reaction equation
[NH2:1][C@@H:2]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:3]([OH:19])[C:4]([N:6]1[CH2:17][C@@H:16]([Cl:18])[CH2:15][C@H:7]1[C:8]([NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5].[CH2:27]([O:34][C:35]([NH:37][C@@H:38]([CH2:42][CH2:43][S:44](=[O:47])(=[O:46])[NH2:45])[C:39](O)=[O:40])=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([O:34][C:35]([NH:37][C@@H:38]([CH2:42][CH2:43][S:44](=[O:46])(=[O:47])[NH2:45])[C:39]([NH:1][C@@H:2]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:3]([OH:19])[C:4]([N:6]1[CH2:17][C@@H:16]([Cl:18])[CH2:15][C@H:7]1[C:8]([NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5])=[O:40])=[O:36])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 20055593N-Cbz-L-2-amino-4-sulfamoylbutyric acidHCID 22872716(4S)-1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide

Product 1

HCID 22872715(4S)-1-{(2S,3S)-3-[2(S)-Benzyloxycarbonylamino-4-sulfamoylbutyryl]amino-2-hydroxy-4-phenylbutyryl}-4-chloro-N-t-butyl-L-prolinamideYield 77.6%

Procedure

Following a procedure similar to that described in Example 66, but using 122 mg (0.32 mmol) of (4S)-1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide [prepared as described in Preparation 21(b)] and 100 mg (0.32 mmol) of (S)-2-benzyloxycarbonylamino-4-sulfamoylbutyric acid, 169 mg of the title compound were obtained as a colorless powder, melting at 115°-122° C.

Sources & evidence

ORD record
ord-95561927527c4b05b0c313c82af5a052
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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