2-(3-{[(Benzyloxy)carbonyl]amino}phenoxy)acetic acid → 1-{(2S,3S)-3-[N2-(3-Benzyloxycarbonylaminophenoxy)acetyl-L--asparaginyl]amino-2-hydroxy-4-phenylbutyryl}-N-t-butyl-L-prolinamide

HRID 1780251Notes

Reaction equation

HRID 1780251 reaction equation
Cl.[NH2:2][C@H:3]([C:8]([NH:10][C@@H:11]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:12]([OH:27])[C:13]([N:15]1[CH2:26][CH2:25][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].[CH2:35]([O:42][C:43]([NH:45][C:46]1[CH:47]=[C:48]([CH:54]=[CH:55][CH:56]=1)[O:49][CH2:50][C:51](O)=[O:52])=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([O:42][C:43]([NH:45][C:46]1[CH:47]=[C:48]([CH:54]=[CH:55][CH:56]=1)[O:49][CH2:50][C:51]([NH:2][C@H:3]([C:8]([NH:10][C@@H:11]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:12]([OH:27])[C:13]([N:15]1[CH2:26][CH2:25][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:52])=[O:44])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 189573862-(3-{[(Benzyloxy)carbonyl]amino}phenoxy)acetic acidHCID 677227821-[(2S,3S)-3-L-asparaginylamino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide hydrochloride

Product 1

HCID 867508221-{(2S,3S)-3-[N2-(3-Benzyloxycarbonylaminophenoxy)acetyl-L--asparaginyl]amino-2-hydroxy-4-phenylbutyryl}-N-t-butyl-L-prolinamideYield 50.2%

Procedure

Following a procedure similar to that described in Example 14, but using 0.45 g (0.91 mmol) of 1-[(2S,3S)-3-L-asparaginylamino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide hydrochloride and 0.30 g (1.00 mmol) of 3-benzyloxycarbonylaminophenoxyacetic acid, 0.34 g of the title compound were obtained as a colorless powder, melting at 107°-117° C.

Sources & evidence

ORD record
ord-1594ba3e8e6e495c9513ad7386328805
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

Loading…