3-(2-(Isopropoxycarbonylamino-methyl)-4-{2-[5-methyl-2-(4-nitro-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid tert-butyl ester → 3-[4-{2-[2-(4-Amino-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester

HRID 1181072Notes

Reaction equation

HRID 1181072 reaction equation
[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:33][NH:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][C:27]([NH2:30])=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:33][NH:34][C:35]([O:37][CH:38]([CH3:39])[CH3:40])=[O:36])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 589793583-(2-(Isopropoxycarbonylamino-methyl)-4-{2-[5-methyl-2-(4-nitro-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 589790083-[4-{2-[2-(4-Amino-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(2-(isopropoxycarbonylamino-methyl)-4-{2-[5-methyl-2-(4-nitro-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid tert-butyl ester (207 mg, 0.365 mmol) and 10% Pd—C (27 mg) in EtOAc (20 mL) was stirred under H2 (1 atm) for 18 h. The reaction mixture was filtered through Celite and concentrated (75° C.) to give the title compound as a colorless oil (196 mg, 100%): MS (ESI) m/z 538 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated (75° C.)

Sources & evidence

ORD record
ord-7277c6b79ba6411cbefa8664f00c5aa8
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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