HCID 54384606, compound → HCID 70253612, compound

HRID 356491Notes

Reaction equation

HRID 356491 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5](=[O:23])[CH2:6][C@:7](O)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[OH-].[Na+]>[OH:23][C:5]1[CH2:6][C@@:7]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:24][C:3](=[O:2])[CH:4]=1

Participants

3

Reactant 1

HCID 54384606HCID 54384606, compound

Product 1

HCID 70253612HCID 70253612, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The title compound was prepared as described in General Method 7 using 0.46 g (1.41 mmol) of (S)-5-hydroxy-3-oxo-5,7-diphenyl-heptanoic acid methyl ester from Example CC and 0.1N NaOH (450 mL). The reaction was stirred for 2 hours at room temperature then extracted with Et2O. The aqueous layer was decanted and acidified with 1N HCL, extracted with EtOAc, dried (MgSO4), and concentrated. Purification by silica gel chromatography, eluting with MeOH:CH2Cl2 (2:98) gave the title compound. 1H NMR (CDCl3) δ 2.25 (m, 2 H), 2.45 (m, 1 H), 2.70 (m, 1 H), 2.92 (dd, 2 H), 3.30 (dd, 2 H), 7.04-7.41 (m, 10 H).

Workup

  1. customThe title compound was prepared
  2. extractionthen extracted with Et2O
  3. customThe aqueous layer was decanted
  4. extractionextracted with EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography
  8. washeluting with MeOH:CH2Cl2 (2:98)

Sources & evidence

ORD record
ord-4695a6a8b5a44cc2822b9a10216c5e81
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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