(4S)-1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide → (4S)-1-[(2S,3S)-3-(2-Benzyloxycarbonylamino-3-dimethylphosphonobutanoyl)amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamide

HRID 1780270Notes

Reaction equation

HRID 1780270 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][CH:38]([CH:42]([P:44]([O:48][CH3:49])([O:46][CH3:47])=[O:45])[CH3:43])[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][CH:38]([CH:42]([P:44]([O:46][CH3:47])([O:48][CH3:49])=[O:45])[CH3:43])[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 22872716(4S)-1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamideHCID 537856222-Benzyloxycarbonylamino-3-dimethylphosphonobutyric acid

Product 1

HCID 22872713(4S)-1-[(2S,3S)-3-(2-Benzyloxycarbonylamino-3-dimethylphosphonobutanoyl)amino-2-hydroxy-4-phenylbutyryl]-4-chloro-N-t-butyl-L-prolinamideYield 25.3%

Procedure

Following a procedure similar to that described in Example 66, but using 115 mg (0.3 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 of 2-benzyloxycarbonylamino-3-dimethylphosphonobutyric acid, and then purifying the product by preparative thin layer chromatography, using a 8:1 by volume mixture of methylene chloride and methanol as the developing solvent, 52 mg of the title compound were obtained as a colorless powder from the upper fraction, melting at 93°-100° C.

Workup

  1. custompurifying the product by preparative thin layer chromatography
  2. additionby volume mixture of methylene chloride and methanol as the developing solvent

Sources & evidence

ORD record
ord-72f026c549df4602b280f6d4af175a38
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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