Acetyl chloride → (1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride
Reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C@@:10]2([NH:15]C(=O)OC(C)(C)C)[CH2:12][C@H:11]2[CH:13]=[CH2:14])=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([Cl:26])(=O)C>CO>[ClH:26].[NH2:15][C@:10]1([C:8]([NH:7][S:4]([CH:1]2[CH2:3][CH2:2]2)(=[O:6])=[O:5])=[O:9])[CH2:12][C@H:11]1[CH:13]=[CH2:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Compound 130 (1 g) was suspended in methanol (2.5 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 131 (833 mg) as a white foam in 103% yield due to DCM.
Workup
- concentrationThe reaction mixture was concentrated at 45-50° C. and co-evaporated with DCM
Sources & evidence
- ORD record
- ord-991e0f923a4c474683a6a7ad6e8c7366
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093379B2
Reaction notes
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