Sodium borohydride → 2-(2-Hydroxy-3-benzyl-5-methyl-cyclohept-4-en-1-yl)-1-oxo-ethyl-valinyl valine methyl ester

HRID 1755809Notes

Reaction equation

HRID 1755809 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C@H:4]([CH:32]([CH3:34])[CH3:33])[NH:5][C:6](=[O:31])[C@H:7]([CH:28]([CH3:30])[CH3:29])[NH:8][C:9](=[O:27])[CH2:10][CH:11]1[CH2:17][CH2:16][C:15]([CH3:18])=[CH:14][CH:13]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]1=[O:26].[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3](=[O:35])[C@H:4]([CH:32]([CH3:34])[CH3:33])[NH:5][C:6](=[O:31])[C@H:7]([CH:28]([CH3:30])[CH3:29])[NH:8][C:9](=[O:27])[CH2:10][CH:11]1[CH2:17][CH2:16][C:15]([CH3:18])=[CH:14][CH:13]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]1[OH:26]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 700844262-(2-Oxo-3-benzyl-5-methyl-cyclohept-4-en-1-yl)-1-oxo-ethyl-valinyl valine methyl ester

Product 1

HCID 700872922-(2-Hydroxy-3-benzyl-5-methyl-cyclohept-4-en-1-yl)-1-oxo-ethyl-valinyl valine methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the above keto-peptide (24) (0.44 g) in ethanol (20 mL) with stirring at room temperature was added NaBH4 (69 mg) in one portion. After stirring for 30 min the reaction was quenched by the addition of aqueous 1N HCl (50 mL). The reaction was extracted with ethyl acetate, washed with saturated NaCl, dried over MgSO4 and evaporated to dryness. The title compound was obtained as a mixture of diastereomers by flash chromatography on silica gel eluted with 60% ethyl acetate in n-hexane then by gravity chromatography in the same system. TLC Rf 0.31 and 0.36 (60% ethyl acetate, n-hexane); MS (DCI/NH3) (M+H)+ =487; 1H NMR (CDCl3)δ0.8-1.0(12H, m) Val γ(CH3)2's, 1.7 (3H, s) allylic CH3, 3.72 (3H, s) CO2CH3, 5.18m and 5.08(1H, br s) vinylic CH, 7.30(5H, s) phenyl.

Workup

  1. customwas quenched by the addition of aqueous 1N HCl (50 mL)
  2. extractionThe reaction was extracted with ethyl acetate
  3. washwashed with saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e88a0ec846574b5183862615baacc604
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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