Trifluoroacetic acid methylene chloride → 1-(Methoxymethyl)cyclopropane-1-sulfonamide

HRID 1815699Notes

Reaction equation

HRID 1815699 reaction equation
C(N[C:6](=[O:8])O)(C)(C)C.COC[NH:12][S:13]([CH:16]1[CH2:18][CH2:17]1)(=[O:15])=[O:14].[C:19](O)(C(F)(F)F)=O.C(Cl)Cl>>[CH3:19][O:8][CH2:6][C:16]1([S:13]([NH2:12])(=[O:14])=[O:15])[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 66752380HCID 66752380, compound

Product 1

HCID 224992771-(Methoxymethyl)cyclopropane-1-sulfonamide

Procedure

Step 15IIe) A solution of 1-methoxy-methylcyclopropylsulfonylamine tert-butylcarbamate (1.14 g, 4.30 mmol) was dissolved in a solution of 50% TFA/CH2Cl2 (30 mL) and was stirred stirred at rt for 16 h. The solvent was removed in vacuo and the residue chromatographed over 80 g of SiO2 (eluting with 0% to 60% EtOAC/Hexanes to afford Example 15, 1-methoxymethylcyclopropylsulfonamide, as a white solid (0.55 g, 77% overall over two steps): 1H NMR (CDCl3) δ 0.95 (m, 2H), 1.44 (m, 2H), 3.36 (s, 3H), 3.65 (s, 2H), 4.85 (s, 2H); 13C NMR (CDCl3) δ 11.17, 40.87, 59.23, 74.80; LRMS m/z 183 (M++NH4).

Workup

  1. stirringstirred at rt for 16 h
  2. customThe solvent was removed in vacuo
  3. customthe residue chromatographed over 80 g of SiO2 (
  4. washeluting with 0% to 60% EtOAC/Hexanes

Sources & evidence

ORD record
ord-735e2ddc35a7460e89eddd1754f07ae6
Source dataset
uspto-grants-2005_04
Patent number
US06878722B2

Reaction notes

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