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

HRID 544836Notes

Reaction equation

HRID 544836 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 was 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 provide the desired product as a hygroscopic, off-white solid (2.60 g, 92%). 1H NMR: (DMSO-d6) δ 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) LC-MS (retention time: 0.24 minutes, method B), 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-dd8b0fdeb63b4acc875c6762cbdca7b6
Source dataset
uspto-grants-2011_05
Patent number
US07935670B2

Reaction notes

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