Trifluoroacetic acid → HCID 11402707, compound

HRID 1091243Notes

Reaction equation

HRID 1091243 reaction equation
C(OC(=O)[NH:7][C:8]([C:11](=[O:16])[N:12]([O:14][CH3:15])[CH3:13])([CH3:10])[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:7][C:8]([CH3:10])([CH3:9])[C:11]([N:12]([O:14][CH3:15])[CH3:13])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 47451638HCID 47451638, compound

Product 1

HCID 11402707HCID 11402707, compoundYield 176%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

The Boc-protected Weinreb amide, [1-(methoxy-methyl-carbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester, (1.1 g, 4.47 mmol), was taken up in TFA/CH2Cl2 (1:1, 50 mL) and stirred for 20 min. Removal of the solvent left 2-amino-N-methoxy-2,N-dimethyl-propionamide (1.15 g, 99%, quantitative yield) as its TFA salt. 1H NMR (200 MHz, CD3OD) δ (ppm): 1.63 (s, 6H), 3.25 (s, 3H), 3.78 (s, 3H). MS (ESI, positive ion): m/z 147.3 (M+1)+.

Workup

  1. customRemoval of the solvent

Sources & evidence

ORD record
ord-6f85c4d974dc4fa5ad7065096d524447
Source dataset
uspto-grants-2012_03
Patent number
US08129355B2

Reaction notes

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