tert-Butanol → HCID 68997226, compound

HRID 660763Notes

Reaction equation

HRID 660763 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][Si:14]([CH3:43])([CH3:42])[CH2:15][CH2:16][O:17][C:18](=[O:41])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:22]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:34]([O:33][C:23]1[CH:22]=[C:21]([O:20][CH2:19][C:18](=[O:41])[O:17][CH2:16][CH2:15][Si:14]([CH3:42])([CH3:43])[CH3:13])[CH:26]=[CH:25][C:24]=1[N:27]([S:2]([NH:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])(=[O:4])=[O:3])[CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 68838279HCID 68838279, compound

Product 1

HCID 68997226HCID 68997226, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To an ice cooled solution of chlorosulfonyl isocyanate (2.55 g, 18 mmol) in methylene chloride (50 mL) is added dropwise a solution of t-butanol (1.33 g, 18 mmol) in methylene chloride (5 mL). The mixture is allowed to wart to RT, stirred for 15 min then re-chilled to 0° C. To this is added dropwise a solution of [3-benzyloxy-4-(methoxycarbonylmethylamino)-phenoxy]-acetic acid 2-trimethylsilanylethyl ester (5.35 g, 12 mmol) and triethylamine (2.07 g, 20.4 mmol) in methylene chloride (15 mL) and the mixture is stirred at RT for 2 h. The mixture is washed with water and the organic phase is dried over NaSO4. The solvent is removed under reduced pressure and the residue is purified by column chromatography to using EtOAc/hexane (3:7) as eluent to give the title compound.

Workup

  1. customis allowed to wart to RT
  2. stirringthe mixture is stirred at RT for 2 h
  3. washThe mixture is washed with water
  4. dry with materialthe organic phase is dried over NaSO4
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-776ac560788640c5850223160dedd333
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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