N-(3-tert-Butyl-phenyl)-4-piperidin-4-yl-benzamide → (1R,2R)-2-{4-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperidine-1-carbonyl}-cyclopentanecarboxylic acid

HRID 2190661Notes

Reaction equation

HRID 2190661 reaction equation
C(O[C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]([OH:18])=[O:17])=[O:10])C1C=CC=CC=1.[C:19]([C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:43])[C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)=[CH:33][CH:32]=2)[CH:26]=[CH:27][CH:28]=1)([CH3:22])([CH3:21])[CH3:20].C(C1C=C(NC(C2C=CC(N3CCN(C([C@H]4CCC[C@@H]4C(O)=O)=O)CC3)=NC=2)=O)C=CC=1)(C)(C)C>>[C:19]([C:23]1[CH:24]=[C:25]([NH:29][C:30]([C:31]2[CH:32]=[CH:33][C:34]([CH:37]3[CH2:38][CH2:39][N:40]([C:9]([C@@H:11]4[CH2:15][CH2:14][CH2:13][C@H:12]4[C:16]([OH:18])=[O:17])=[O:10])[CH2:41][CH2:42]3)=[CH:35][CH:36]=2)=[O:43])[CH:26]=[CH:27][CH:28]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 3

HCID 59317976N-(3-tert-Butyl-phenyl)-4-piperidin-4-yl-benzamideHCID 59317991(1S,2S)-2-{4-[5-(3-tert-butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclopentanecarboxylic acidHCID 66738585(1s,2s)-2-(Benzyloxycarbonyl)cyclopentanecarboxylic acid

Product 1

HCID 59318034(1R,2R)-2-{4-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperidine-1-carbonyl}-cyclopentanecarboxylic acid

Procedure

(1R,2R)-2-{4-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperidine-1-carbonyl}-cyclopentanecarboxylic acid was synthesized from (1S,2S)-cyclopentane-1,2-dicarboxylic acid monobenzyl ester and N-(3-tert-butyl-phenyl)-4-piperidin-4-yl-benzamide in a manner similar to the one described in the synthesis of (1S,2S)-2-{4-[5-(3-tert-butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclopentane-carboxylic acid above. LCMS calcd for C29H36N2O4 (m/e) 476, obsd 477 (M+H).

Sources & evidence

ORD record
ord-dc7396bc5ad742fca2ea22ea68140c4d
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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