Sodium Hydroxide → HCID 69210030, compound

HRID 902912Notes

Reaction equation

HRID 902912 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 MHz: 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-da08c527f8cb40a592d1680dbfc086b4
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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