3-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid → N-[(1S,2S,4R)-1-Benzyl-4-(2-cyclohexylethylcarbamoyl)-2-hydroxypentyl]-3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide

HRID 1612501Notes

Reaction equation

HRID 1612501 reaction equation
OC1C=C(C=C(N2CCCC2=O)C=1)C(O)=O.[CH2:17]([C@H:24]([NH:41][C:42](=[O:59])[C:43]1[CH:48]=[C:47]([N:49]2[CH2:53][CH2:52][CH2:51][C:50]2=[O:54])[CH:46]=[C:45]([O:55][CH:56]([CH3:58])[CH3:57])[CH:44]=1)[C@@H:25]([OH:40])[CH2:26][C@H:27]([C:29](=[O:39])[NH:30][CH2:31][CH2:32][C:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=1)[CH3:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([C@H:24]([NH:41][C:42](=[O:59])[C:43]1[CH:48]=[C:47]([N:49]2[CH2:53][CH2:52][CH2:51][C:50]2=[O:54])[CH:46]=[C:45]([O:55][CH:56]([CH3:58])[CH3:57])[CH:44]=1)[C@@H:25]([OH:40])[CH2:26][C@H:27]([C:29](=[O:39])[NH:30][CH2:31][CH2:32][CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1)[CH3:28])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 222530273-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acidHCID 69589915N-[(1S,2S,4R)-1-Benzyl-4-(cyclohex-1-enylethylcarbamoyl)-2-hydroxypentyl]-3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide

Product 1

HCID 58583639N-[(1S,2S,4R)-1-Benzyl-4-(2-cyclohexylethylcarbamoyl)-2-hydroxypentyl]-3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to D6 (hydrogenation stage) from N-[(1S,2S,4R)-1-benzyl-4-(cyclohex-1-enylethylcarbamoyl)-2-hydroxypentyl]-3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide (D51).

Sources & evidence

ORD record
ord-ffc58ff06a5049ae91fcf7ad3d432f5a
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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