HCID 22458236, compound → HCID 21341099, compound

HRID 2185545Notes

Reaction equation

HRID 2185545 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:15][C:16]([O:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:25]([C@@H:27]1[C@@H:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:30][N:29]([C@H:38]([CH:51]2[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)[C:39]([O:41]CC2C=CC(OC)=CC=2)=[O:40])[CH2:28]1)=O>>[CH2:8]([NH:15][C:16]([O:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C@@H:27]2[C@@H:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:30][N:29]([C@H:38]([CH:51]3[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]3)[C:39]([OH:41])=[O:40])[CH2:28]2)[CH2:21][CH2:20]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 22458236HCID 22458236, compoundHCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 21341099HCID 21341099, compoundYield 64%

Procedure

The title compound was prepared from 4-((N-benzylcarbamoyl)oxy)-piperidine trifluoroacetate (35 mg, 0.1 mmol, from Step B) and (R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, 4-(methoxy)benzyl ester (25 mg, 0.05 mmol, Aldehyde 5) according to the method described in Example 1, Step C to give 17 mg (64%) of the title compound. ESI-MS: 534.5 (M+H); HPLC A: 2.16 min.

Sources & evidence

ORD record
ord-9cf74b34e4d848d68d45806fff79c6d4
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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