Acetic Acid → 4-[(1R)-2-({6-[4-(1,1-Dioxido-3,4-dihydro-2H-thiochromen-7-yl)butoxy]hexyl}amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol formate

HRID 1593036Notes

Reaction equation

HRID 1593036 reaction equation
C[C:2]1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:38])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:35]=[C:34]4[C:29]([CH2:30][CH2:31][CH2:32][S:33]4(=[O:37])=[O:36])=[CH:28][CH:27]=3)=[CH:11][C:5]=2[CH2:4][O:3]1.C(O)(=[O:42])C>O>[CH:2]([O:7][C:6]1[CH:8]=[CH:9][C:10]([C@@H:12]([OH:38])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:35]=[C:34]3[C:29]([CH2:30][CH2:31][CH2:32][S:33]3(=[O:36])=[O:37])=[CH:28][CH:27]=2)=[CH:11][C:5]=1[CH2:4][OH:42])=[O:3]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 69442949(1R)-1-(2,2-Dimethyl4H-1,3-benzodioxin-6-yl)-2-({6-[4-(1,1-dioxido-3,4-dihydro-2H-thiochromen-7-yl)butoxy]hexyl}amino)ethanol

Product 1

HCID 878371884-[(1R)-2-({6-[4-(1,1-Dioxido-3,4-dihydro-2H-thiochromen-7-yl)butoxy]hexyl}amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol formate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (1R)-1-(2,2-dimethyl4H-1,3-benzodioxin-6-yl)-2-({6-[4(1,1-dioxido-3,4-dihydro-2H-thiochromen-7-yl)butoxy]hexyl}amino)ethanol (134 mg) in glacial acetic acid (10 ml) and water (5 ml) was heated at 80° C. for 40 min. The mixture was concentrated in vacuo and the residue purified by mass directed autoprep to give the title compound (79 mg). LCMS RT=2.46 min, ES+ve 520 (MH)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by mass

Sources & evidence

ORD record
ord-ac820dfdf19f4b8a9693d8ab7158ee72
Source dataset
uspto-grants-2007_11
Patent number
US07294650B2

Reaction notes

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