tert-Butanol → HCID 67138315, compound

HRID 1592025Notes

Reaction equation

HRID 1592025 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:28])[CH2:16][NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[O:26][CH3:27]>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:28])[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:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanateHCID 28570573HCID 28570573, compound

Product 1

HCID 67138315HCID 67138315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1.15 g (8.08 mmol) of chlorosulfonyl isocyanate in 10 mL of CH2Cl2 is added dropwise a solution of 598 mg (8.08 mmol) of t-butanol in 2 mL of CH2Cl2. The solution is stirred at RT for 45 min, then a solution of 1.3 g (5.8 mmol) of the title A compound, (2,4-dimethoxyphenylamino)-acetic acid methyl ester and 1.2 g (11.9 mmol) of TEA in 4 mL of CH2Cl2 is added dropwise. The mixture is stirred at RT for 90 min, then washed with water. The organic phase is dried over anhydrous Na2SO4 and the solvent is removed under reduced pressure. The residual oil is purified by chromatography using 10% EtOAc in CH2Cl2 as the eluant to give N-(t-butoxycarbonylsulfamoyl)-N-(2,4-dimethoxy-phenyl)glycine methyl ester as a thick yellow oil: 1H-NMR (CDCl3) δ 7.57 (d, J=9.19, 1H), 7.19 (s, 1H), 6.51-6.46 (m, 2H), 4.55 (br s, 2H), 3.82 (s, 3H), 3.80 (s, 3H), 3.71 (s, 3H), 1.53 (s, 9H); [M−1]−=403.

Workup

  1. stirringThe mixture is stirred at RT for 90 min
  2. washwashed with water
  3. dry with materialThe organic phase is dried over anhydrous Na2SO4
  4. customthe solvent is removed under reduced pressure
  5. customThe residual oil is purified by chromatography

Sources & evidence

ORD record
ord-63ce5b858e2842e69cbd8660b853c93f
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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