Water → HCID 9909906, compound

HRID 1007581Notes

Reaction equation

HRID 1007581 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 86591244HCID 86591244, compound

Product 1

HCID 9909906HCID 9909906, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (1.46 g, 0.0105 mol, 3 eq) was added to a solution of 5a (1.49 g, 0.0035 mol, 1 eq) in methanol (15 mL) (see FIGS. 2 and 3). The suspension was stirred under nitrogen for 2 h. Water (200 mL) was added and the suspension was extracted with ethyl acetate (200 mL). The organic solution was washed with brine (100 mL), separated and dried over sodium sulfate. Evaporation of the solvent afforded the methyl ester 6a as a solid (1.17 g, 87% yield). Rf 0.30 (hexane/EtOAc=8:2). 1H NMR δ (CDCl3) 0.70 (d, 3H), 1.25 (s, 3H), 1.51 (d, 1H), 1.94 (m, 1H), 2.20-2.50 (m, 3H), 2.60-3.00 (m, 5H), 3.55 (s, 3H), 6.64 (d, 2H), 6.75 (s, 1H), 6.85 (s, 1H), 7.10-7.35 (m, 7H); [M+H]+382.2,: tR=3.42 min; purity: 99%. (Chiral purity determination; HPLC conditions: column Chiralcel OD 4.6×250 mm; flow: 1 mL/min; mobile phase: 92.5% hexane/7.5% isopropanol; λ=254 nM; Inj. Vol: 20 μL; 6a (reference standard): tR=27.97 min; 6b (reference standard): tR=25.36 min; result: 6a/6b=98.7/1.3 (% area pic calculation)].

Workup

  1. extractionthe suspension was extracted with ethyl acetate (200 mL)
  2. washThe organic solution was washed with brine (100 mL)
  3. customseparated
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f63d700c6d554125a586d96af5d2f55c
Source dataset
uspto-grants-2004_09
Patent number
US06794510B2

Reaction notes

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