N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethyl-butylcarbamoyl)-2-hydroxypenty]-3,5-bis-(2-oxo-pyrrolidin-1-yl)benzamide → 3-Acetylamino-N-[(1S,2S,4R)-1-benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-5-(2-oxopyrrolidin-1-yl)benzamide

HRID 1612483Notes

Reaction equation

HRID 1612483 reaction equation
[CH2:1]([C@H:8]([NH:23][C:24](=[O:43])[C:25]1[CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[CH:28]=[C:27]([N:37]2CC[CH2:39][C:38]2=[O:42])[CH:26]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17](C)([CH3:19])[CH3:18])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:44](NC1C=C(C=C(N2CCCC2=O)C=1)C(O)=O)(=O)[CH3:45].C12CC(CC1)CC2NC(=O)[C@H](C)C[C@H](O)[C@@H](N)CC1C=CC=CC=1>>[C:38]([NH:37][C:27]1[CH:26]=[C:25]([CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[CH:28]=1)[C:24]([NH:23][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH:15]1[CH2:16][CH:17]2[CH2:18][CH:44]1[CH2:45][CH2:19]2)[CH3:12])=[O:43])(=[O:42])[CH3:39]

Participants

4

Reactant 3

HCID 10196800N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethyl-butylcarbamoyl)-2-hydroxypenty]-3,5-bis-(2-oxo-pyrrolidin-1-yl)benzamideHCID 222530043-Acetylamino-5-(2-oxopyrrolidin-1-yl)benzoic acidHCID 68889549(2R,4S,5S)-5-Amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amide

Product 1

HCID 585836533-Acetylamino-N-[(1S,2S,4R)-1-benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxypentyl]-5-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to E5, from 3-acetylamino-5-(2-oxopyrrolidin-1-yl)benzoic acid (D13) and (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amide (D29).

Sources & evidence

ORD record
ord-54002531340d4de4ade441ef0eea9fb1
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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