Sodium Hydroxide → HCID 11247328, compound

HRID 130504Notes

Reaction equation

HRID 130504 reaction equation
C([O:3][C:4]([C@:6]1([NH2:30])[C@H:11]([S:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)(=[O:14])=[O:13])[CH2:10][C@@H:9]2[C@H:7]1[C@@:8]2([F:29])[C:24]([O:26]CC)=[O:25])=[O:5])C.[OH-].[Na+]>S(=O)(=O)(O)O>[NH2:30][C@@:6]1([C:4]([OH:5])=[O:3])[C@H:11]([S:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)(=[O:14])=[O:13])[CH2:10][C@@H:9]2[C@H:7]1[C@@:8]2([F:29])[C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11271615HCID 11271615, compound

Product 1

HCID 11247328HCID 11247328, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

108 mg of (1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester was stirred in 1.08 mL of 60% sulfuric acid (W/V %) for 3 days at 130° C. The reaction solution was ice-cooled and then neutralized in an aqueous solution of 5N sodium hydroxide. The mixture was stirred for 1 hour at room temperature and then purified by ion exchange resin (AG 50W-X8 Resin (H form), eluent: water, a 30% aqueous solution of tetrahydrofuran and a 10% aqueous solution of pyridine), thereby yielding 76 mg of (1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfonyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid.

Workup

  1. temperaturecooled
  2. custompurified by ion exchange resin (AG 50W-X8 Resin (H form), eluent

Sources & evidence

ORD record
ord-78e22aa51b804b57ad0cb864cae78982
Source dataset
uspto-grants-2008_06
Patent number
US07381746B2

Reaction notes

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