4-(n-(n-Benzylcarbamoyl)-n-(prop-1-yl)amino)-piperidine trifluoroacetate → 2-(R)-(3-(S)-(4-(N-(N-Benzylcarbamoyl)-N-(prop-1-yl)amino)piperidin-1-yl)methyl-4-(S)-phenyl-pyrrolidin-1-yl)-2(cyclohexyl)acetic acid

HRID 2185551Notes

Reaction equation

HRID 2185551 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:15][C:16]([N:18]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH2:19][CH2:20][CH3:21])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[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>>[CH2:8]([NH:15][C:16]([N:18]([CH:22]1[CH2:23][CH2:24][N:25]([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)[CH2:26][CH2:27]1)[CH2:19][CH2:20][CH3:21])=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 224582694-(n-(n-Benzylcarbamoyl)-n-(prop-1-yl)amino)-piperidine trifluoroacetateHCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 213411042-(R)-(3-(S)-(4-(N-(N-Benzylcarbamoyl)-N-(prop-1-yl)amino)piperidin-1-yl)methyl-4-(S)-phenyl-pyrrolidin-1-yl)-2(cyclohexyl)acetic acidYield 40%

Procedure

The title compound was prepared from 4-(N-(N-benzylcarbamoyl)-N(prop-1-yl)amino)-piperidine trifluoroacetate (19 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 6.4 mg (40%) of the title compound. ESI-MS: 575.4 (M+H); HPLC A: 2.32 min.

Sources & evidence

ORD record
ord-a62ace6bf1db44cc87224b269edded4d
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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