Triethylamine → Methyl 3-[(2-tert-butoxy-2-oxo-1-phenylethyl)sulfamoyl]benzoate

HRID 1529530노트

반응식

HRID 1529530 반응식
[C:1]([O:5][C:6](=[O:15])[CH:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[S:17]([C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:19])=[O:18].C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6](=[O:15])[CH:7]([NH:14][S:17]([C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:19])=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 113339Benzoic acid, 3-(chlorosulfonyl)-, methyl esterHCID 12162441HCID 12162441, 화합물

생성물 1

HCID 86720693Methyl 3-[(2-tert-butoxy-2-oxo-1-phenylethyl)sulfamoyl]benzoate수율 43.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of tert-butyl-2-amino-2-phenylacetate (1.34 g, 6.45 mmol) and methyl 3-(chlorosulfonyl)benzoate (1.53 g, 6.51 mmol) in tetrahydrofuran (15 mL) was added triethylamine (0.90 mL, 6.45 mmol) in one portion at ambient temperature. The reaction mixture was stirred for 30 minutes, after which time, the reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate (30 mL) and 10% citric acid solution (10 mL). The resulting organic phases were dried over magnesium sulfate and concentrated under reduced pressure to yield a crude solid. The solid was triturated in diethyl ether (5 mL) and cold methanol (5 mL) to yield the title compound as a white solid (1.13 g, 43%).

후처리

  1. concentrationafter which time, the reaction mixture was concentrated under reduced pressure
  2. custompartitioned between ethyl acetate (30 mL) and 10% citric acid solution (10 mL)
  3. dry with materialThe resulting organic phases were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto yield a crude solid
  6. customThe solid was triturated in diethyl ether (5 mL)

출처 및 근거

ORD 기록
ord-7d85209e3f1244728aa3851869eca2c7
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090606B2

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