Sodium Hydroxide → HCID 87663962, compound

HRID 2055061Notes

Reaction equation

HRID 2055061 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([C@:17]([C@H:21]([C@@H:30]([C@@H:39]([CH2:41][O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[OH:40])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([OH:20])C=O)(=[O:16])C.[OH-].[Na+]>C1COCC1.CO>[C:8]1([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1.[CH2:23]([O:22][C@@H:21]([C@@H:30]([C@@H:39]([CH2:41][O:42][CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[OH:40])[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C@@H:17]([OH:20])[CH:14]=[O:16])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 87664320HCID 87664320, compound

Product 1

HCID 87663962HCID 87663962, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (CXII) (802 mg, 1.37 mmol) in 10 mL of THF is added MeOH (20 mL) and 12 drops of a saturated methanolic solution of NaOH. The reaction is stirred overnight then diluted with 150 mL of MeOH. Amberlite acidic resin is added and the reaction is stirred for 10 minutes. Litmus paper indicates that the pH is neutral and the resin is filtered off. The filtrate is concentrated in vacuo and the residue is purified by flash chromatography (20% EtOAc/petroleum ether to give 654 mg (93%) of the β sulfide (CXIII), and 49 mg (7%) of the a sulfide as white solids. Rf(β)=0.20 (15% EtOAc/petroleum ether) Rf(α)=0.13 (15% EtOAc/petroleum ether); 1H NMR (β) (CDCl3, 500 MHz) δ 7.25-7.63 (m, 20H), 4.87-4.98 (m, 3H), 4.55-4.68 (m, 4H), 3.85 (dd, J=11.0, 1.5 Hz, 1H), 3.79 (dd, J=10.5, 4.5 Hz, 1H), 3.63-3.68 (m, 2H), 3.54-3.60 (m, 2H), 2.50 (s, 1H, free OH); 13C NMR (β) (CDCl3, 500 MHz) δ 139.2, 139.0, 138.8, 133.6, 132.6, 129.7, 129.3, 129.2, 129.1, 128.8, 128.7, 128.5, 128.4, 128.3.

Workup

  1. additionAmberlite acidic resin is added
  2. stirringthe reaction is stirred for 10 minutes
  3. filtrationthe resin is filtered off
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is purified by flash chromatography (20% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-c381b26401bf4bd88c0a3d988e450553
Source dataset
uspto-grants-2008_02
Patent number
US07331920B2

Reaction notes

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