tert-Butanol → HCID 68839874, compound

HRID 660811Notes

Reaction equation

HRID 660811 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].[C:13]1([S:19]([C:22]2[CH:27]=[CH:26][C:25]([NH:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[C:24]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:23]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:33][O:32][C:30](=[O:31])[CH2:29][N:28]([S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[C:25]1[CH:26]=[CH:27][C:22]([S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])=[CH:23][C:24]=1[O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 86632591HCID 86632591, compound

Product 1

HCID 68839874HCID 68839874, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
2.5 °C

Procedure

To a solution of chlorosulfonylisocyanate (346 mg, 2.45 mmol) in CH2Cl2 (15 mL) at 0° C. is added dropwise a solution of t-butanol (181 mg, 2.45 mmol) in CH2Cl2 (5 mL) and the mixture is stirred at 0-5° C. for 30 min. To this is added dropwise a solution of methyl (4-benzenesulfonyl-2-benzyloxyphenylamino)acetate (620 mg, 1.63 mmol) and triethylamine (281 mg, 278 mmol) in CH2Cl2 (5 mL) and the mixture is stirred at RT for 4 h. The mixture is washed with water and the organic layer is dried over magnesium sulfate. The solvent is removed under reduced pressure to afford an oil that is chromatographed on a Biotage 40M column using CH2Cl2/EtOAc (95:5) as eluent to afford the title compound as an oil: 1H NMR (CDCl3) δ 7.82 (m, 3H), 7.47 (m, 11H), 5.24 (s, 2H), 4.54 (br s, 2H), 3.67 (s, 3H), 1.41 (s, 9H); (M−1)−=589.

Workup

  1. stirringthe mixture is stirred at RT for 4 h
  2. washThe mixture is washed with water
  3. dry with materialthe organic layer is dried over magnesium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customto afford an oil that
  6. customis chromatographed on a Biotage 40M column

Sources & evidence

ORD record
ord-9b740c4df31e44b29f1c2e274c735b14
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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