Dimethyl Sulfide → N-{1-[(1-Formyl-2-methyl-propyl)-methyl-carbamoyl]-2,2-dimethyl-propyl}-3-methyl-2-methylamino-3-phenyl-butyramide

HRID 1865720

Reaction equation

HRID 1865720 reaction equation
[CH3:1][NH:2][C@H:3]([C:13]([NH:15][C@H:16]([C:21]([N:23]([C@@H:25]([CH:32]([CH3:34])[CH3:33])/[CH:26]=C(/C(O)=O)\C)[CH3:24])=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:14])[C:4]([CH3:12])([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[O:35]=[O+][O-].CSC>CO>[CH:26]([CH:25]([N:23]([CH3:24])[C:21]([CH:16]([NH:15][C:13](=[O:14])[CH:3]([NH:2][CH3:1])[C:4]([CH3:12])([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:11])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:22])[CH:32]([CH3:33])[CH3:34])=[O:35]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823Ozone2×HCID 6918637N,beta,beta-Trimethyl-L-phenylalanyl-N-((1S,2E)-3-carboxy-1-(1-methylethyl)-2-buten-1-yl)-N,3-dimethyl-L-valinamide

Product 1

HCID 72370856N-{1-[(1-Formyl-2-methyl-propyl)-methyl-carbamoyl]-2,2-dimethyl-propyl}-3-methyl-2-methylamino-3-phenyl-butyramide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of N,β,β-trimethyl-L-phenylalanyl-N1-[(1S,2E)-3-carboxy-1-isopropylbut-2-enyl]-N1,3-dimethyl-L-valinamide (1.0 g) in methanol (20 mL) is added to 100 mL of methanol at −78° C. which had been treated with ozone until the solution is blue. The resulting colorless reaction mixture is treated with ozone at −78° C. until the blue color remained. After 5 min dimethylsulfide (2 mL) is added. The reaction mixture is allowed to warm to room temperature and then concentrated in vacuo to give the title compound as an oil. MS (ES): m/z 418.4 (M+H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3dc5eca9edd46a29983ee0d6b6f4469
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Linked notes

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