HCID 67151507, compound → HCID 67151495, compound

HRID 1805216Notes

Reaction equation

HRID 1805216 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pt](=O)=O>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67151507HCID 67151507, compound

Product 1

HCID 67151495HCID 67151495, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a stirred suspension of (S)-4-((E)-2-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (57 mg) in methanol (8 ml) was added platinum(IV) oxide (14 mg) and the mixture was then stirred under an atmosphere of hydrogen at room temperature for 1 hour. The mixture was then filtered through celite and the filtrate was concentrated in vacuo to afford (S)-4-(2-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (60 mg, quant) as an off-white solid. MS (ISP): 476.2 ([{37Cl}M−H]+), 474.3 ([{35Cl}M−H]+), 420.2 ([{37Cl}M+H—C4H8]+), 418.3 ([{35Cl}M+H—C4H8]+).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-de597f8fd65c4f7187b4153e50e179b0
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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