Water → HCID 71246713, compound

HRID 1519074Notes

Reaction equation

HRID 1519074 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:9])[CH2:8][CH2:7]1)=[O:5].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:2][O:3][C:4]([C:6]1([NH:9][S:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[Br:10])(=[O:19])=[O:18])[CH2:8][CH2:7]1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5204032-Bromobenzenesulfonyl chlorideHCID 12760695Methyl 1-aminocyclopropane-1-carboxylate hydrochloride

Product 1

HCID 71246713HCID 71246713, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

methyl-1-aminocyclopropanecarboxylate hydrochloride (300 mg, 1.979 mmol) was dissolved in CH2Cl2 (7 ml), added with 2-bromobenzene-1-sulfonyl chloride (550 mg, 2.17 mmol) and triethylamine (1.1 ml, 7.92 mmol), and stirred at room temperature for 12 hours. The resultant solution was added with H2O, extracted with CH2Cl2 (×2), dried with MgSO4, and filtered. Through vacuum distillation, the solvent was removed. The resultant mixture was purified with column chromatography so as to obtain methyl-1-(2-bromophenylsulfonamido)cyclopropanecarboxylate (560 mg, 1.68 mmol, 85%).

Workup

  1. extractionextracted with CH2Cl2 (×2)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. distillationThrough vacuum distillation
  5. customthe solvent was removed
  6. customThe resultant mixture was purified with column chromatography so as

Sources & evidence

ORD record
ord-9dd5a9ba989f487ca9759f4874066713
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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