Lithium hydroxide, monohydrate → HCID 12020408, compound

HRID 1835569Notes

Reaction equation

HRID 1835569 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C@:9]1([F:26])[C@@H:14]2[C@H:10]1[CH:11]=[CH:12][C@@:13]2([NH2:25])[C:15]([O:17]CC1C=CC=CC=1)=[O:16])=[O:8])C>O.O1CCCC1>[NH2:25][C@@:13]1([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][C@@H:10]2[C@H:14]1[C@@:9]2([F:26])[C:7]([OH:8])=[O:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12020407HCID 12020407, compound

Product 1

HCID 12020408HCID 12020408, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate, in an amount of 25 mg, dissolved in 5 mL of water was added to 90 mg of (1R,2S,5R,6R)-2-amino-6-fluoro-bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester dissolved in 2 mL of tetrahydrofuran, and the mixture was stirred for 2 hours at room temperature. The solvent was concentrated under reduced pressure. The residue was purified by ion exchange resin (AG 50W-X8 Resin (H type), eluent: water, a 50% aqueous solution of tetrahydrofuran, and a 10% aqueous solution of pyridine), thereby yielding 24 mg of (1R,2S,5R,6R)-2-amino-6-fluoro-bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylic acid.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customThe residue was purified by ion exchange resin (AG 50W-X8 Resin (H type), eluent

Sources & evidence

ORD record
ord-47eda0e8bfc34c6da833b39231773d81
Source dataset
uspto-grants-2004_08
Patent number
US06770676B2

Reaction notes

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