(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid → AHPBA 36a

HRID 1780241Notes

Reaction equation

HRID 1780241 reaction equation
C(O[C:6]([N:8]1[CH2:19][CH2:18][C@H:17]([OH:20])[C@H:9]1[C:10]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])(C)(C)C.[CH2:21]([O:28][C:29]([NH:31][C@H:32]([C:37]([NH:39][C@@H:40]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C@H:41]([OH:45])C(O)=O)=[O:38])[CH2:33][C:34](=[O:36])[NH2:35])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([O:28][C:29]([NH:31][C@H:32]([C:37]([NH:39][C@@H:40]([CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[C@H:41]([OH:45])[C:6]([N:8]1[CH2:19][CH2:18][C@H:17]([OH:20])[C@H:9]1[C:10]([NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:7])=[O:38])[CH2:33][C:34](=[O:36])[NH2:35])=[O:30])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 57125825(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acidHCID 70050913(3S)-1-t-Butoxycarbonyl-3-hydroxy-N-t-butyl-L-prolinamide

Product 1

HCID 473133AHPBA 36aYield 65.4%

Procedure

Following a procedure similar to that described in Example 11, 28 mg (0.10 mmol) of (3S)-1-t-butoxycarbonyl-N-t-butyl-3-hydroxy-L-prolinamide (prepared as described in Preparation 13) was deprotected to remove the t-butoxycarbonyl group. The resulting (3S)-N-t-butyl-3-hydroxy-L-prolinamide was then condensed with 52 mg (0.12 mmol) of (2S,3S)-3-(N2 -benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid (prepared as described in Preparation 1), to give 40 mg of the title compound as a white powder, melting at 111°-113° C.

Workup

  1. customto remove the t-butoxycarbonyl group

Sources & evidence

ORD record
ord-b7fe11a8373046769435504174e9248e
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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