Isopropanol → 4-{4-[2-(4-Methanesulfonyl-phenyl)-1-methyl-ethylamino]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 10202Notes

Reaction equation

HRID 10202 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[CH:24]([CH3:25])[CH:23]([C:26]3[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=3)OC2=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(C)C.C([O-])=O.[K+]>O.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH:24]([CH3:25])[CH2:23][C:26]2[CH:27]=[CH:28][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:30][CH:31]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 2735122Potassium FormateHCID 692257874-{4-[5-(4-Methanesulfonyl-phenyl)-4-methyl-2-oxo-oxazolidin-3-yl]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 692236474-{4-[2-(4-Methanesulfonyl-phenyl)-1-methyl-ethylamino]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl esterYield 97.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 10 g 4-{4-[5-(4-methanesulfonyl-phenyl)-4-methyl-2-oxo-oxazolidin-3-yl]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester, 1 g of 20% palladium hydroxide on carbon, 10 ml water, and 90 ml isopropanol was stirred and heated to 50°–60° C. A solution of 3.5 g potassium formate in 5 ml water was slowly added. The mixture was stirred for 3 hours and was then cooled and filtered. The filtrate was stripped to yield ca. 9 g of 4-{4-[2-(4-methanesulfonyl-phenyl)-1-methyl-ethylamino]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureheated to 50°–60° C
  2. stirringThe mixture was stirred for 3 hours
  3. temperaturewas then cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8cc838779d1549c48ac94421ceba2821
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Reaction notes

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