Acetic Acid → 4-{(1R)-2-[(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol acetate

HRID 2118328Notes

Reaction equation

HRID 2118328 reaction equation
[CH:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][C@@H:28]([C:30]3[CH:41]=[CH:40][C:33]4[O:34][C:35]([CH3:39])(C)[O:36][CH2:37][C:32]=4[CH:31]=3)[OH:29])[CH:12]=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(O)=[O:44]>O>[C:35]([O:34][C:33]1[CH:40]=[CH:41][C:30]([C@@H:28]([OH:29])[CH2:27][NH:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][CH2:16][CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([S:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)(=[O:7])=[O:8])[CH:10]=2)=[CH:31][C:32]=1[CH2:37][OH:44])(=[O:36])[CH3:39]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 69119807(1R)-2-[(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Product 1

HCID 692039264-{(1R)-2-[(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of (1R)-2-[(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (110 mg) in glacial AcOH (5 ml) and water (0.3 ml) was heated at 85° C. for 40 min. The solution was evaporated to dryness and the residue was purified by Biotage™ column chromatography on silica using DCM-EtOH-ammonia (50:8:1) as eluent. The residue was dissolved in MeOH, treated with glacial AcOH and the solvent was removed to give the title compound (76 mg). LCMS RT=2.6 min ES+ve 548

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue was purified by Biotage™ column chromatography on silica
  3. dissolutionThe residue was dissolved in MeOH
  4. additiontreated with glacial AcOH
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-26138c4a703c441788d334680d5d8f3a
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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