tert-Butanol → HCID 66756685, compound

HRID 1642600Notes

Reaction equation

HRID 1642600 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 6344DichloromethaneSolvent2×

Procedure

To an ice cooled solution of chlorosulfonyl isocyanate (0.788 mL, 8.94 mmol) in DCM (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 DCM-(40 mL) is added dropwise. After stirring for 30 min., DCM (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-0537be8ff6ab4f1ea53481dfe795ed96
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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