Sodium Bicarbonate → HCID 11224264, compound

HRID 658529Notes

Reaction equation

HRID 658529 reaction equation
Cl.C(OCC)(=O)C.[CH2:8]([O:10][C:11]([C@:13]1([NH:35]C(OC(C)(C)C)=O)[C@H:18]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:17][C@@H:16]2[C@H:14]1[C@@:15]2([F:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:12])[CH3:9].C(=O)([O-])O.[Na+]>>[CH2:8]([O:10][C:11]([C@:13]1([NH2:35])[C@H:18]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:17][C@@H:16]2[C@H:14]1[C@@:15]2([F:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:12])[CH3:9]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 66628528HCID 66628528, compound

Product 1

HCID 11224264HCID 11224264, compoundYield 92.3%

Procedure

2.8 mL of a 4N hydrogen chloride/ethyl acetate solution was added to 28 mg of (1R,2R,3R,5R,6R)-2-t-butoxycarbonylamino-3-(3,4-dichlorobenzylamino)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester, and the mixture was stirred for 6 hours at ice-cooling, and further stirred for 18 hours at room temperature. The reaction solution was ice-cooled, and then neutralized with a saturated aqueous solution of sodium hydrogen carbonate, followed by separation. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure, thereby yielding 21 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylamino)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

Workup

  1. temperaturecooling
  2. stirringfurther stirred for 18 hours at room temperature
  3. temperaturecooled
  4. customfollowed by separation
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter the desiccant was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-53adb01dbae540c49fdb6bd9d41cf833
Source dataset
uspto-grants-2011_12
Patent number
US08076502B2

Reaction notes

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