Hydrochloric Acid → Cyclopropanecarboxamide, 1-amino-2-ethenyl-N-[(1-methylcyclopropyl)sulfonyl]-, hydrochloride (1:1), (1R,2S)-

HRID 1481642Notes

Reaction equation

HRID 1481642 reaction equation
C(OC(=O)[NH:7][C@:8]1([C:13](=[O:22])[NH:14][S:15]([C:18]2([CH3:21])[CH2:20][CH2:19]2)(=[O:17])=[O:16])[CH2:10][C@H:9]1[CH:11]=[CH2:12])(C)(C)C.[ClH:24]>O1CCOCC1>[ClH:24].[NH2:7][C@:8]1([C:13]([NH:14][S:15]([C:18]2([CH3:21])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[O:22])[CH2:10][C@H:9]1[CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56605353tert-butyl [(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]carbamate

Product 1

HCID 66650595Cyclopropanecarboxamide, 1-amino-2-ethenyl-N-[(1-methylcyclopropyl)sulfonyl]-, hydrochloride (1:1), (1R,2S)-Yield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl((1R,2S)-1-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamate (40 g, 116 mmol) in 4 N HCl in dioxane (400 mL) was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure and the residue was washed with diethyl ether to get crude compound (31 g, 95%). The crude compound was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.97-9.29 (m, 2H), 5.47-5.66 (m, 1H), 5.32-5.44 (m, 1H), 5.22 (dd, J=10.04, 1.51 Hz, 1H), 2.38 (s, 1H), 2.03 (s, 1H), 1.71 (d, J=3.51 Hz, 1H), 1.46-1.52 (m, 4H), 1.25-1.35 (m, 1H), 0.88-1.01 (m, 2H). MS: MS m/z 245.14 (M++1).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-a5c9b50649dd452b95f053667ab0ef63
Source dataset
uspto-grants-2016_08
Patent number
US09409943B2

Reaction notes

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