HCID 22458270, compound → HCID 21341087, compound

HRID 2185557Notes

Reaction equation

HRID 2185557 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:12][C:13]([N:15]([CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH2:16][CH3:17])=[O:14].[CH:28]([C@@H:30]1[C@@H:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:33][N:32]([C@H:41]([CH:54]2[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]2)[C:42]([O:44]CC2C=CC(OC)=CC=2)=[O:43])[CH2:31]1)=O>>[F:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:12][C:13]([N:15]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:28][C@@H:30]2[C@@H:34]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:33][N:32]([C@H:41]([CH:54]3[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]3)[C:42]([OH:44])=[O:43])[CH2:31]2)[CH2:20][CH2:19]1)[CH2:16][CH3:17])=[O:14]

Participants

3

Reactant 2

HCID 22458270HCID 22458270, compoundHCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 21341087HCID 21341087, compoundYield 54.4%

Procedure

The title compound was prepared from 4-(N-((3,4-difluorobenzyl)carbonyl)-N-ethylamino)piperidine trifluoroacetate (40 mg, 0.1 mmol, from Step A) and 2-(R)-(3-(R)-formyl-4-(S)-phenyl-pyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, 4-(methoxy)benzyl ester (25 mg, 0.06 mmol, Aldehyde 5) according to the method described in Example 1, Step C to give 19 mg (54%) of the title compound. ESI-MS: 582.5 (M+H); HPLC A: 2.35 min.

Sources & evidence

ORD record
ord-020154ff62ad41f28980d2fdfd517d25
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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