Hydrochloric Acid → HCID 66628602, compound

HRID 1665895Notes

Reaction equation

HRID 1665895 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-cb22860922424d17a23078e0ca1e2db0
Source dataset
uspto-grants-2011_10
Patent number
US08039647B2

Reaction notes

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