Sodium Hydroxide → HCID 69210030, compound

HRID 2214240Notes

Reaction equation

HRID 2214240 reaction equation
C([O:3][C:4](=[O:37])[CH:5]([CH2:14][CH2:15][CH2:16][S:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C.[OH-].[Na+]>CO.O>[C:10]([O:9][C:7](=[O:8])[CH2:6][CH:5]([CH2:14][CH2:15][CH2:16][S:17][C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:4]([OH:37])=[O:3])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69211802HCID 69211802, compound

Product 1

HCID 69210030HCID 69210030, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the compound of example 28 (3.00 g, 5.78 mmol) in methanol (30 mL) and water (10 mL) was added NaOH (1N, 11.6 mL, 11.6 mmol). The mixture was stirred vigorously under ambient conditions. After 24 hours, most of the methanol has evaporated. The residue was portioned between water and ether. The water phase was extracted two times with ether, then acidified with HCl (1N) to pH 1. The water phase was extracted three times with ethyl acetate. The recombined organic phase was dried over sodium sulfate, filtered, and evaporated. The residue was flashed using 5% methanol in chloroform to give the product as a white solid. 1H-NMR(CDCl3, 400 MH: 1.45(s, 9H); 1.35–1.64(m, 4H); 1.58(m, 1H); 2.16(m, 2H); 2.26(m, 1H); 2.64(m, 1H); 4.12(q, J=7.1 Hz, 2H), 7.19–7.29, 7.40(m, 15H).

Workup

  1. custommost of the methanol has evaporated
  2. extractionThe water phase was extracted two times with ether
  3. extractionThe water phase was extracted three times with ethyl acetate
  4. dry with materialThe recombined organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9147cb75a0fe44d581049af8512bf071
Source dataset
uspto-grants-2006_09
Patent number
US07105539B2

Reaction notes

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