tert-Butanol → N-(t-butoxycarbonylsulfamoyl)-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester

HRID 643952ノート

反応式

HRID 643952 の反応式
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[CH3:13][O:14][C:15](=[O:39])[CH2:16][NH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:24][C:23](=[O:36])[C:22]([O:37][CH3:38])=[CH:21]2.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:13][O:14][C:15](=[O:39])[CH2:16][N:17]([S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:24][C:23](=[O:36])[C:22]([O:37][CH3:38])=[CH:21]2

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 86624027(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-ylamino)-acetic acid methyl ester

生成物 1

HCID 86624028N-(t-butoxycarbonylsulfamoyl)-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of chlorosulfonyl isocyanate (0.15 mL, 1.75 mmol) in 4 mL of CH2Cl2, cooled in a ice bath, is added t-butanol (0.17 mL, 1.75 mmol). The mixture is warmed to ambient temperature and stirred for 15 min. The solution is cooled in an ice bath and a solution of (7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-ylamino)-acetic acid methyl ester (0.430 g, 1.17 mmol) and triethylamine (0.35 mL, 2 mmol) is added dropwise. After addition is complete, the mixture is warmed to ambient temperature and stirred for 1.5 h. To this is added water (1 mL) and the mixture is extracted with EtOAc. The organic layer is washed with water, sat. NaCl and dried over sodium sulfate. The solvent is removed under reduced pressure to afford N-(t-butoxycarbonylsulfamoyl)-N-(7-benzyloxy-3-methoxy-2-oxo-2H-chromen-6-yl)glycine methyl ester as a white solid: 1H NMR (CDCl3) δ 7.78 (s, 1H), 7.71 (s, 1H), 7.38-7.30 (m, 5H), 6.82, (s, 1H), 6.78 (s, 1H), 5.18 (s, 2H), 4.55 (s, 2H), 3.83 (s, 3H); 3.66 (s, 3H), 1.41 (s, 9H); (M+H)+=549.

後処理

  1. temperatureThe solution is cooled in an ice bath
  2. additionAfter addition
  3. temperaturethe mixture is warmed to ambient temperature
  4. stirringstirred for 1.5 h
  5. extractionthe mixture is extracted with EtOAc
  6. washThe organic layer is washed with water, sat. NaCl
  7. dry with materialdried over sodium sulfate
  8. customThe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-4e44a4ef47af4328acf9f1487114ace3
出典データセット
uspto-grants-2010_04
特許番号
US07700633B2

反応ノート

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