3-Acetoxybenzoic acid → HCID 67300177, compound

HRID 1016124Notes

Reaction equation

HRID 1016124 reaction equation
Cl.[NH2:2][C@H:3]([CH:19]([CH3:21])[CH3:20])[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5].[C:22]([O:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](O)=[O:30])(=[O:24])[CH3:23]>>[C:22]([O:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:28]([C:29](=[O:30])[NH:2][C@H:3]([CH:19]([CH3:21])[CH3:20])[C:4]([N:6]2[CH2:11][CH2:10][CH:9]([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)[CH2:8][CH2:7]2)=[O:5])[CH:27]=1)(=[O:24])[CH3:23]

Participants

3

Reactant 2

HCID 2386693-Acetoxybenzoic acidHCID 67299489HCID 67299489, compound

Product 1

HCID 67300177HCID 67300177, compoundYield 50%

Procedure

(R)-2-Amino-1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methylbutan-1-one hydrochloride was coupled with 3-acetoxy benzoic acid in a similar manner as described for the preparation of Example 75 to give (R)-3-((1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamoyl)phenyl acetate (115 mg, 50% yield). MS found: 457.3 (M+).

Workup

  1. customas described for the preparation of Example 75

Sources & evidence

ORD record
ord-b17520fe50b04fbfacd94228cace7492
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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