tert-Butanol → HCID 66756685, compound

HRID 660475Notes

Reaction equation

HRID 660475 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]([O:17][C:18](=[O:36])[CH2:19][NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>C(Cl)Cl>[C:13]([O:17][C:18](=[O:36])[CH2:19][N:20]([S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 66756652HCID 66756652, compound

Product 1

HCID 66756685HCID 66756685, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To an ice cooled solution of chlorosulfonyl isocyanate (0.788 mL, 8.94 mmol) in methylene chloride (40 mL) is added dropwise t-butanol (0.855 mL, 8.94 mmol). Then at 0° C., (2-benzyloxy-4-iodophenylamino)-acetic acid tert-butyl ester (2.62 g, 5.96 mmol) and triethylamine (2.08 mL, 14.9 mmol) in methylene chloride (40 mL) is added dropwise. After stirring for 30 min, methylene chloride (300 mL) is added and the organic layer is washed with 2N HCl solution. It is then dried with NaSO4, and concentrated. The residue is purified by column chromatography to give the title compound as an off-white foam.

Workup

  1. washthe organic layer is washed with 2N HCl solution
  2. dry with materialIt is then dried with NaSO4
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-c488a8854e3f45d2990de591885ca8c9
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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