Benzoic acid, 4-amino-, 1,1-dimethylethyl ester → tert-Butyl 4-({7-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-7-oxoheptyl}amino)benzoate

HRID 446535Notes

Reaction equation

HRID 446535 reaction equation
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:29])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]O)[CH3:19])[CH2:12][CH2:11]1.[NH2:36][C:37]1[CH:49]=[CH:48][C:40]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:39][CH:38]=1>>[C:1]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([CH3:19])[C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:36][C:37]2[CH:49]=[CH:48][C:40]([C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])=[CH:39][CH:38]=2)[CH2:12][CH2:11]1)=[O:29]

Participants

3

Reactant 2

HCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 666716911-{2-[(7-Hydroxyheptanoyl)(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

Product 1

HCID 123736591tert-Butyl 4-({7-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-7-oxoheptyl}amino)benzoateYield 52%

Procedure

The compound (94 mg, 0.195 mmol) obtained in Example 39b was used to give a crude aldehyde compound according to the method described in Example 4g. The resulting crude aldehyde compound and tert-butyl 4-aminobenzoate (62 mg, 0.293 mmol) were used to give the title compound (66 mg; yield, 52%) as a white solid according to the method described in Example 18b.

Workup

  1. customto give a crude aldehyde compound

Sources & evidence

ORD record
ord-2e7646ba5c4c4f23a618561e646665ec
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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