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

HRID 420083Notes

Reaction equation

HRID 420083 reaction equation
[CH3:1][C:2]1([S:5]([NH:8][C:9]([C@@:11]2([NH:16]C(=O)OC(C)(C)C)[CH2:13][C@H:12]2[CH:14]=[CH2:15])=[O:10])(=[O:7])=[O:6])[CH2:4][CH2:3]1.C([Cl:27])(=O)C>CO>[ClH:27].[NH2:16][C@:11]1([C:9]([NH:8][S:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)(=[O:7])=[O:6])=[O:10])[CH2:13][C@H:12]1[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 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 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Compound 122 (51.5 g) was suspended in methanol (150 mL). A solution of acetyl chloride (3 eq.) in methanol was added to the suspension. The reaction mixture was heated at 50° C. for 3 hrs. The reaction mixture was concentrated at 45-50° C. and co-evaporated with DCM to give compound 123 (42.4 g) as a white powder in 102% yield due to DCM.

Workup

  1. concentrationThe reaction mixture was concentrated at 45-50° C. and co-evaporated with DCM

Sources & evidence

ORD record
ord-464b54fd0f9647a3b4da838828b1999f
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

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