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

HRID 643952Notes

Reaction equation

HRID 643952 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4e44a4ef47af4328acf9f1487114ace3
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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