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

HRID 2252624Notes

Reaction equation

HRID 2252624 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) 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-29602423036b487d874d2542dc006d8f
Source dataset
uspto-grants-2008_01
Patent number
US07323447B2

Reaction notes

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