Sodium Hydroxide → HCID 67797893, compound

HRID 1491996Notes

Reaction equation

HRID 1491996 reaction equation
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C@H:9]2[CH2:13][O:12][C@H:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C@@H:10]2[CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:2]=[CH:3][C:4]([CH2:7][O:8][C@H:9]2[CH2:13][O:12][C@H:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C@@H:10]2[CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67797507HCID 67797507, compound

Product 1

HCID 67797893HCID 67797893, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 28.2 g (0.0597 mol) of methyl (Z)-(2S,3S,4R)-7-[4-(1,1'-biphenyl-4-ylmethoxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-4-heptenoate, 433 ml of methanol and 172.8 ml (0.173 mmol) of 1N sodium hydroxide is stirred at 45° C. for two h and at room temperature for 11/2 h. The solvent is evaporated, the residue is taken up in water and extracted twice with ethyl ether. The aqueous layer is adjusted to pH 5.5 and extracted with ethyl acetate (3×10 ml). The combined extracts are washed with brine, dried (MgSO4), evaporated and the residue is crystallized from methylene chloride and ether to give (Z)-(2S,3S,4R)-7-[4-(1,1'-biphenyl-4-ylmethoxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-4-heptenoic acid, having mp. 96°-98° C. and [α]D 25=+98.58 (MeOH).

Workup

  1. customThe solvent is evaporated
  2. extractionextracted twice with ethyl ether
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. washThe combined extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customthe residue is crystallized from methylene chloride and ether

Sources & evidence

ORD record
ord-283d195b4c714c8990cc0307b5ee947f
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

Loading…