Ethyl Acetate → HCID 67490866, compound

HRID 1917324Notes

Reaction equation

HRID 1917324 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[C:13]([O:17][C:18]([NH:20][C@@:21]12[CH2:27][CH2:26][C@:25]1([CH2:28][O:29][CH3:30])[CH2:24][N:23]([C@@H:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:32])[C:22]2=O)=[O:19])([CH3:16])([CH3:15])[CH3:14].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[C:13]([O:17][C:18]([NH:20][C@@:21]12[CH2:27][CH2:26][C@:25]1([CH2:28][O:29][CH3:30])[CH2:24][N:23]([C@@H:31]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH3:32])[CH2:22]2)=[O:19])([CH3:14])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 2724148Sodium potassium tartrate tetrahydrateHCID 16684438Red-AlHCID 67491024HCID 67491024, compound

Product 1

HCID 67490866HCID 67490866, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A 65% solution of Red-Al™ in toluene (1.43 mL, 4.75 mmol) was added dropwise to a solution of (1S,5S)-1-(tert-butoxycarbonylamino)-5-methoxymethyl-2-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.2.0]heptane (593 mg, 1.58 mmol) in toluene in a nitrogen atmosphere at 0° C. over two minutes. The mixture was heated to room temperature, stirred for two hours, and cooled to 0° C. A 20% potassium sodium tartrate tetrahydrate solution (10 mL) was carefully added while maintaining the internal temperature of the reaction solution at 10° C. or less. The reaction solution was poured into a mixture of ethyl acetate (10 mL) and brine (10 mL), followed by extraction with ethyl acetate (100 mL). The organic layer was washed with brine (20 mL), and then dried over anhydrous sodium sulfate and filtered. The filtrate was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→9:1) to give 244 mg (43%) of the title compound as colorless crystals.

Workup

  1. temperaturecooled to 0° C
  2. temperaturewhile maintaining the internal temperature of the reaction solution at 10° C. or less
  3. extractionfollowed by extraction with ethyl acetate (100 mL)
  4. washThe organic layer was washed with brine (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was then concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→9:1)

Sources & evidence

ORD record
ord-e8f13f707dd846e19b5627764d584879
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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