Phosphate → (1R)-2-{[2-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 916826Notes

Reaction equation

Br[CH2:2][CH2:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[CH:6][CH:5]=1.[NH2:18][CH2:19][C@@H:20]([C:22]1[CH:33]=[CH:32][C:25]2[O:26][C:27]([CH3:31])([CH3:30])[O:28][CH2:29][C:24]=2[CH:23]=1)[OH:21].P([O-])([O-])([O-])=O>CN(C=O)C>[NH3:18].[Si:9]([O:8][C:7]1[CH:16]=[CH:17][C:4]([CH2:3][CH2:2][NH:18][CH2:19][C@@H:20]([C:22]2[CH:33]=[CH:32][C:25]3[O:26][C:27]([CH3:30])([CH3:31])[O:28][CH2:29][C:24]=3[CH:23]=2)[OH:21])=[CH:5][CH:6]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of [4-(2-bromoethyl)phenoxy](tert-butyl)dimethylsilane (479 mg) in DMF (20 ml) under nitrogen was treated with (1R)-2-amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (678 mg) and the mixture was stirred at 20° C. for 9.5 h. Phosphate buffer solution (pH 6.5) was added and the mixture was extracted with EtOAc. The extract was washed with water and dried (Na2SO4). Solvent evaporation in vacuo gave a residue which was purified by SPE (10 g). Elution with DCM then DCM-EtOH-0.880 ammonia solution (300:8:1) then (150:8:1) gave the title compound (991 mg). LCMS RT=3.13 min.

Workup

extractionthe mixture was extracted with EtOAc
washThe extract was washed with water
dry with materialdried (Na2SO4)
customSolvent evaporation in vacuo
customgave a residue which
customwas purified by SPE (10 g)
washElution with DCM

Sources & evidence

ORD record: ord-f47181a2c3224d86a8f8c2923de2290c
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271197B2

Reaction notes

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