Ethyl Acetate → HCID 58787870, compound

HRID 1375916Notes

Reaction equation

HRID 1375916 reaction equation
C([O:3][C:4](=O)[C@@:5]([NH:25]C(OC(C)(C)C)=O)([CH3:24])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)C.[BH4-].[Li+].C(OCC)(=O)C>C(OCC)C>[NH2:25][C@:5]([CH3:24])([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][CH2:22][CH3:23])=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[CH2:4][OH:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 58787888HCID 58787888, compound

Product 1

HCID 58787870HCID 58787870, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (R)-2-tert-butoxycarbonylamino-4-(4′-butyl-biphenyl-4-yl)-2-methyl-butyric acid ethyl ester (22 mg) in diethylether is added lithium borohydride (20 mg). After stirring the suspension for 9 h at RT, ethyl acetate (5 ml) is added and the mixture is washed with water (2 ml), 1M citric acid (2×2 ml) and water (2 ml). The organic phase is dried over MgSO4, the solvent removed and the crude material purified by chromatography using diethyl ether/hexane (1/1) (Rf=0.31, MS: (ES+): 412.6 (M+H)+). The purified product is dissolved in dioxane containing 4M HCl and left at room temperature for 16 h. After lyophilisation, the desired compound is obtained as a white solid in the hydrochloride salt form (Rf=0.48 in DCM/methanol 100/15, MS: (ES+): 312.5 (M+H)+).

Workup

  1. washthe mixture is washed with water (2 ml), 1M citric acid (2×2 ml) and water (2 ml)
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent removed
  4. customthe crude material purified by chromatography
  5. dissolutionThe purified product is dissolved in dioxane containing 4M HCl
  6. waitleft at room temperature for 16 h

Sources & evidence

ORD record
ord-4fcf091dd3fa4a8abde5a538f5b1ebf4
Source dataset
uspto-grants-2007_01
Patent number
US07169817B2

Reaction notes

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