Hydrochloric Acid → HCID 22618714, compound

HRID 842274Notes

Reaction equation

HRID 842274 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([NH:24][C:25]([O:27][CH3:28])=[O:26])([CH3:23])C(OCC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].Cl.O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]1([CH3:23])[CH2:28][O:27][C:25](=[O:26])[NH:24]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 22618725HCID 22618725, compound

Product 1

HCID 22618714HCID 22618714, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(2-benzyloxyphenyl)-2-methoxycarbonylamino-2-methylbutanoate (5.2 g) in tetrahydrofuran (135 ml), under a nitrogen atmosphere, lithium borohydride (0.59 g) was added and the mixture was refluxed under heating for an hour. Then, a 2N hydrochloric acid (6.6 ml) was added thereto and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure to give the subject compound (4.6 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for an hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution
  5. dry with materiala saturated brine and dried over sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-807451b7222f4154af48a2ea8602344b
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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