Sodium Methoxide → HCID 52913496, compound

HRID 1944105Notes

Reaction equation

HRID 1944105 reaction equation
C([O:4][C@@H:5]1[C@@H:12]([O:13]C(=O)C)[C@H:11]([O:17]C(=O)C)[C:8]2([CH2:10][CH2:9]2)[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]3[O:37][CH2:36][CH2:35][NH:34][C:33]=3[CH:38]=2)[CH:22]=1)(=O)C.C[O-].[Na+]>CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C@H:6]2[C@H:5]([OH:4])[C@@H:12]([OH:13])[C@H:11]([OH:17])[C:8]3([CH2:10][CH2:9]3)[O:7]2)=[CH:22][C:23]=1[CH2:28][C:29]1[CH:30]=[CH:31][C:32]2[O:37][CH2:36][CH2:35][NH:34][C:33]=2[CH:38]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 52913601HCID 52913601, compound

Product 1

HCID 52913496HCID 52913496, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of acetic acid (5S,6S,7R,8S)-6,7-diacetoxy-5-[4-chloro-3-(3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-4-oxa-spiro[2.5]oct-8-yl ester (100 mg, 0.18 mmol) in methanol (6 mL) was added sodium methoxide (39 mg, 0.73 mmol) and stirred at room temperature for 3 h. The solvent was evaporated and crude product purified by silica gel column chromatography to give 35 mg of (5S,6R,7R,8S)-5-[4-chloro-3-(3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol as a white solid.

Workup

  1. customThe solvent was evaporated
  2. customcrude product purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3d53487ca2aa4c1bb7f5230d451e35ee
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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