Sodium Methoxide → HCID 52914600, compound

HRID 1944082Notes

Reaction equation

HRID 1944082 reaction equation
C([O:4][C@H:5]1[C@H:12]([O:13]C(=O)C)[C:9]2([CH2:11][CH2:10]2)[O:8][C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[CH:18]=2)[C@@H:6]1[O:32]C(=O)C)(=O)C.C[O-].[Na+]>CO>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C@H:7]2[C@H:6]([OH:32])[C@@H:5]([OH:4])[C@H:12]([OH:13])[C:9]3([CH2:11][CH2:10]3)[O:8]2)=[CH:18][C:19]=1[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 52914599HCID 52914599, compound

Product 1

HCID 52914600HCID 52914600, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Acetic acid (5S,6S,7R,8S)-7,8-diacetoxy-5-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-6-yl ester (60 mg, 0.1 mmole) in dry methanol (3 mL), sodium methoxide (3 mg) was added at room temperature and stirred for overnight. Reaction mixture evaporated to dryness. The crude product was purified by preparative HPLC to furnish 25 mg of (5S,6R,7R,8S)-5-[4-Chloro-3-(4-hydroxy-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol.

Workup

  1. customReaction mixture
  2. customevaporated to dryness
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-326f5068bcd24b4cb36704d984406a3e
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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