Trifluoroacetic acid → 2(S)-Amino-N-methoxy-3,3,N-trimethyl-butyramide

HRID 2084531Notes

Reaction equation

HRID 2084531 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13](=[O:18])[N:14]([O:16][CH3:17])[CH3:15])[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl.CO>[NH2:7][C@@H:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:13]([N:14]([O:16][CH3:17])[CH3:15])=[O:18]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53879830[1(S)-(Methoxy-methyl-carbamoyl)-2,2-dimethylpropyl]-carbamic Acid-tert-butyl Ester

Product 1

HCID 213052842(S)-Amino-N-methoxy-3,3,N-trimethyl-butyramideYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [1(S)-(methoxy-methyl-carbamoyl)-2,2-dimethylpropyl]-carbamic acid-tert-butyl ester (1.686 g, 6.15 mmol) in dichloromethane (20 mL) at 0° C. was added trifluoroacetic acid (17 mL). The reaction was allowed to stand for 16 hours at <5° C. before the solvents were removed in vacuo to give a bright yellow oil. The residue was dissolved in methanol (30 mL) and was treated portionwise with Dowex 1X8-400 basic resin until pH 9. Filtration and removal of the solvents in vacuo gave the title compound as a pale yellow oil (990 mg, 92%). The material was used without further purification.

Workup

  1. customwere removed in vacuo
  2. customto give a bright yellow oil
  3. additionwas treated portionwise with Dowex 1X8-400 basic resin until pH 9
  4. filtrationFiltration and removal of the solvents in vacuo

Sources & evidence

ORD record
ord-08baaf0223bf4ada945bc3f594f77e93
Source dataset
uspto-grants-2004_04
Patent number
US06716878B1

Reaction notes

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