HCID 22458231, compound → HCID 21341103, compound

HRID 2185549Notes

Reaction equation

FC(F)(F)C(O)=O.[N+:8]([C:11]1[CH:30]=[CH:29][C:14]([CH2:15][NH:16][C:17]([N:19]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:20][CH2:21][CH3:22])=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9].[CH:31]([C@@H:33]1[C@@H:37]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:36][N:35]([C@H:44]([CH:57]2[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]2)[C:45]([O:47]CC2C=CC(OC)=CC=2)=[O:46])[CH2:34]1)=O>>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH:16][C:17]([N:19]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:31][C@@H:33]3[C@@H:37]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH2:36][N:35]([C@H:44]([CH:57]4[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]4)[C:45]([OH:47])=[O:46])[CH2:34]3)[CH2:25][CH2:24]2)[CH2:20][CH2:21][CH3:22])=[O:18])=[CH:29][CH:30]=1)([O-:10])=[O:9]

Participants

Reactant 2

HCID 22458231HCID 22458231, compound

HCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 21341103HCID 21341103, compoundYield 63.4%

Procedure

The title compound was prepared from 4-(N-(N-(4-nitrobenzyl)carbamoyl)-N-(prop-1-yl)amino)-piperidine trifluoroacetate (21 mg, 0.048 mmol, from Step A) and 2-(R)-(3-(R)-formyl-4-(S)-phenyl-pyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, (4-methoxy)benzyl ester (14 mg, 0.028 mmol, Aldehyde 5) according to the method described in Example 1, Step C to give 11 mg (63%) of the title compound. ESI-MS: 620.4 (M+H); HPLC A: 2.33 min.

Sources & evidence

ORD record: ord-d8848103c20e41ba8f120be94490a1c6
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06399619B1

Reaction notes

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