Hydrochloric Acid → HCID 66628602, compound

HRID 2380859Notes

Reaction equation

HRID 2380859 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C@:9]1([F:33])[C@@H:14]2[C@H:10]1[CH2:11][C@@H:12]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=1)[C@@:13]2([NH2:22])[C:15]([O:17][CH:18]([CH2:20][CH3:21])[CH3:19])=[O:16])=[O:8])C.Cl>O1CCCC1.O>[CH3:19][CH:18]([O:17][C:15]([C@:13]1([NH2:22])[C@H:12]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:11][C@@H:10]2[C@H:14]1[C@@:9]2([F:33])[C:7]([OH:8])=[O:6])=[O:16])[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66628105HCID 66628105, compound

Product 1

HCID 66628602HCID 66628602, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

15 mg of lithium hydroxide monohydrate was added to 131 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-butyl ester 6-ethyl ester dissolved in 2 mL of tetrahydrofuran and 1 mL of water, and the mixture was stirred for 1.5 hours at room temperature. After 2 mL of 1N hydrochloric acid was added thereto, the reaction solution was concentrated under reduced pressure, and the obtained residue was purified by reverse phase chromatography (Wako gel 50C18 (made by Wako Pure Chemical Industries Ltd.) eluent:water to a 40% acetonitrile solution), thereby yielding 37 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-butyl ester.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe obtained residue was purified by reverse phase chromatography (Wako gel 50C18 (made by Wako Pure Chemical Industries Ltd.) eluent

Sources & evidence

ORD record
ord-fea8a9cfc2dd4be6bc9fcc2609fb2618
Source dataset
uspto-grants-2012_09
Patent number
US08258133B2

Reaction notes

Loading…