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

HRID 2118325Notes

Reaction equation

HRID 2118325 reaction equation
[CH:1]1([S:6]([C:8]2[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][C@@H:27]([C:29]3[CH:40]=[CH:39][C:32]4OC(C)(C)[O:35][CH2:36][C:31]=4[CH:30]=3)[OH:28])[CH:11]=[CH:12][CH:13]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:41]([OH:44])(=[O:43])[CH3:42]>O>[C:41]([O:44][C:32]1[CH:39]=[CH:40][C:29]([C@@H:27]([OH:28])[CH2:26][NH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][CH2:15][CH2:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([S:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[CH:9]=2)=[CH:30][C:31]=1[CH2:36][OH:35])(=[O:43])[CH3:42]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 69119885(1R)-2-[(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Product 1

HCID 691199214-{(1R)-2-[(6-{4-[3-(Cyclopentylsulfinyl)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-(cyclopentylsulfinyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (0.1 g) in glacial acetic acid (5 ml) and water (0.2 ml) was heated at 82° C. for 40 min. The solution was evaporated to dryness to give the title compound as a clear oil (0.075 g). LCMS=2.61 min, ES+ve 532 (MH+).

Workup

  1. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-528f07e83432444cb76cdac4c0fe12b1
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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