Triethylamine → HCID 67367499, compound

HRID 2387925Notes

Reaction equation

HRID 2387925 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH2:11][CH2:10]1.[CH3:17][O:18][C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([S:26](Cl)(=[O:28])=[O:27])=[C:21]([CH3:30])[CH:20]=1>ClCCl>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH3:30])[C:22]([S:26]([NH:8][C:9]2([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH2:11][CH2:10]2)(=[O:27])=[O:28])=[C:23]([CH3:25])[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1502033Methyl 1-aminocyclobutane-1-carboxylateHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Product 1

HCID 67367499HCID 67367499, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Triethylamine (13.9 mmol, 2.0 equiv.) was added at 0° C. to a solution of methyl 1-aminocyclobutanecarboxylate (6.97 mmol, 1 equiv.) in dichloromethane p.a. (20 ml), and the mixture was stirred for 10 minutes. 4-Methoxy-2,6-dimethyl-phenylsulfonyl chloride (8.36 mmol, 1.2 equiv.), dissolved in DCM (5 ml), was slowly added dropwise at the same temperature, and the mixture was stirred for 4 hours at 25° C. The reaction mixture was diluted with dichloromethane (100 ml), washed with distilled water (2×50 ml) and saturated sodium chloride solution (2×50 ml) and dried over sodium sulfate. The solvent was concentrated and the crude product was purified by column chromatography (15% ethyl acetate in hexane) to yield the desired product in the form of a white solid. Yield: 66%

Workup

  1. additionwas slowly added dropwise at the same temperature
  2. stirringthe mixture was stirred for 4 hours at 25° C
  3. washwashed with distilled water (2×50 ml) and saturated sodium chloride solution (2×50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solvent was concentrated
  6. customthe crude product was purified by column chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-80496e1f2bfa44f897847546e4bb7aac
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

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