Water → HCID 10596019, compound

HRID 1007582Notes

Reaction equation

HRID 1007582 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:12]=[C:13]([C@:17]2([CH3:37])[CH2:22][CH2:21][N:20]([CH2:23][C@@H:24]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:25]([O:27][CH3:28])=[O:26])[CH2:19][C@@H:18]2[CH3:36])[CH:14]=[CH:15][CH:16]=1)(=O)C.O>CO>[OH:10][C:11]1[CH:12]=[C:13]([C@:17]2([CH3:37])[CH2:22][CH2:21][N:20]([CH2:23][C@@H:24]([CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:25]([O:27][CH3:28])=[O:26])[CH2:19][C@@H:18]2[CH3:36])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86591245HCID 86591245, compound

Product 1

HCID 10596019HCID 10596019, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (0.156 g, 0.001 mol, 3 eq) was added to a solution of 5b (0.160 g, 0.0003 mol, 1 eq) in methanol (15 mL). The suspension was stirred under nitrogen for 2 h. Water (50 mL) was added and the suspension was extracted with ethyl acetate (100 mL). The organic solution was washed with brine (50 mL), separated and dried over sodium sulfate. Evaporation of the solvent afforded the methyl ester 6b as a solid (0.060 g, 41% yield). Rf 0.30 (hexane/EtOAc=8:2). 1H NMR δ (CDCl3) 0.73 (d, 3H), 1.26 (s, 3H), 1.51 (d, 1H), 1.94 (m, 1H), 2.20-2.35 (m, 2H), 2.40-2.50 (m, 2H), 2.55-2.70 (m, 2H), 2.80-3.00 (m, 3H), 3.58 (s, 3H), 6.60 (d, 1H), 6.75 (s, 1H), 6.85 (d, 1H), 7.10-7.30 (m, 7H).

Workup

  1. extractionthe suspension was extracted with ethyl acetate (100 mL)
  2. washThe organic solution was washed with brine (50 mL)
  3. customseparated
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c90e78fb609140619d03100e6c271811
Source dataset
uspto-grants-2004_09
Patent number
US06794510B2

Reaction notes

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