Citric Acid → HCID 66975425, compound

HRID 1022573Notes

Reaction equation

HRID 1022573 reaction equation
[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]2[CH2:20][O:19][CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:15]2[C:28](OCC)=[O:29])[CH:10]=[CH:11][C:12]=1[Cl:13].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCO>[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]2[CH2:20][O:19][CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH:15]2[CH2:28][OH:29])[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 66975558HCID 66975558, compound

Product 1

HCID 66975425HCID 66975425, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of sodium borohydride (49 mg) in THF (1.25 mL)-EtOH (0.9 mL) was added calcium chloride (72 mg), and the mixture was stirred at room temperature for 20 min. To this reaction mixture was added a solution of 4-tert-butyl 5-ethyl (5RS,6SR)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4,5-dicarboxylate (135 mg) in THF (1.25 ml), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was poured into 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (118 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8f5415cf90ee48d383d92a11e99d131b
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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