Methanol → HCID 21957279, compound

HRID 2213170Notes

Reaction equation

HRID 2213170 reaction equation
C([O:4][CH:5]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]#[CH:20])=[C:13]([O:21][CH3:22])[CH:12]=1)=[S:7])(=O)C.[OH-].[Na+].CO>O>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([CH:5]([OH:4])[C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]#[CH:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[S:7])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21957298HCID 21957298, compound

Product 1

HCID 21957279HCID 21957279, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-acetoxy-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-thioacetamide (compound A1.03; 0.603 g), sodium hydroxide (1.4 ml 1 n solution in water) and methanol (5 ml) is stirred for 6 hours at room temperature. Water (30 ml) is added. The reaction mixture is extracted with ethyl acetate (2×100 ml). The organic layers are washed with brine (20 ml), dried and the solvent is evaporated. 2-(4-Chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-thioacetamide is obtained which is purified by flash-column-chromatography on silica gel using ethyl acetate/hexane, yielding a resin, 1H-NMR (300 MHz, CDCl3, δ(ppm)): 2.5(t, 1H), 2.9(t, 2H), 3.8(s, 3H), 3.85–4.05(m, 2H), 4.25 (s, 1H), 4.75(d, 2H), 5.1(s, 1H), 6.5(dd, 1H), 6.65(d, 1H), 6.9(d, 1H), 7.2(d, 2H), 7.3(d, 2H), 7.7–7.8(m, 1H).

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate (2×100 ml)
  2. washThe organic layers are washed with brine (20 ml)
  3. customdried
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-e84e02f4d2554d438139f5c89cbe0d7e
Source dataset
uspto-grants-2006_09
Patent number
US07105545B2

Reaction notes

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