Water → HCID 71247066, compound

HRID 1519084Notes

Reaction equation

HRID 1519084 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:11])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[Cl:12][C:13]1[C:14]([CH3:23])=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:2][O:3][C:4]([C:6]1([NH:11][S:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[C:14]=2[CH3:23])(=[O:20])=[O:21])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HCl

Product 1

HCID 71247066HCID 71247066, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

methyl-1-aminocyclopentanecarboxylate hydrochloride (300 mg, 1.67 mmol) was dissolved in CH2Cl2 (7 ml), added with 3-chloro-2-methylbenzene-1-sulfonyl chloride (413 mg, 1.83 mmol) and triethylamine (0.9 ml, 6.68 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-(3-chloro-2-methylphenylsulfonamido)cyclopentanecarboxylate (554 mg, 1.67 mmol, 90%).

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-38f9ec7605d24bcc8a5ecf74c74092cd
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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