Dichloromethane → (1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride

HRID 1797792Notes

Reaction equation

HRID 1797792 reaction equation
C(OC([NH:8][C@:9]1([C:14]([NH:16][S:17]([CH:20]2[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[O:15])[CH2:11][C@H:10]1[CH:12]=[CH2:13])=O)(C)(C)C.[Cl:23]CCl>C(O)(C(F)(F)F)=O>[ClH:23].[NH2:8][C@:9]1([C:14]([NH:16][S:17]([CH:20]2[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[O:15])[CH2:11][C@H:10]1[CH:12]=[CH2:13]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 45480526Carbamic acid, N-[(1R,2S)-1-[[(cyclopropylsulfonyl)amino]carbonyl]-2-ethenylcyclopropyl]-, 1,1-dimethylethyl ester

Product 1

HCID 23595124(1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product of Step 2 (3.5 g, 10.6 mmol) in dichloromethane (35 mL) and TFA (32 mL) was stirred at room temperature for 1.5 hours. The volatiles were removed in vacuo and the residue suspended in 1N HCl in diethyl ether (20 mL) and concentrated in vacuo. This procedure was repeated once. The resulting mixture was triturated from pentane and filtered to give the title compound as a hygroscopic, off-white solid (2.60 g, 92%). 1H NMR: (DMSO-d6) 1.01-1.15 (m, 4H), 1.69-1.73 (m, 1H), 1.99-2.02 (m, 1H), 2.38 (q, J=9 Hz, 1H), 2.92-2.97 (m, 1H), 5.20 (d, J=11 Hz, 1H), 5.33 (d, J=17 Hz, 1H), 5.52-5.59 (m, 1H), 9.17 (br s, 3H); MS m/z 231 (M++H).

Workup

  1. customThe volatiles were removed in vacuo
  2. concentrationconcentrated in vacuo
  3. customThe resulting mixture was triturated from pentane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-4a965e8fa45c4fbeb1dc82ffd40d8848
Source dataset
uspto-grants-2013_01
Patent number
US08343477B2

Reaction notes

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