Sodium borohydride → 2-(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-hydroxy-cyclohept-4-en-1-yl)-1-oxo-ethyl-valinyl-valine methyl ester

HRID 1755819Notes

Reaction equation

HRID 1755819 reaction equation
[CH3:1][O:2][C:3](=[O:47])[C@H:4]([CH:44]([CH3:46])[CH3:45])[NH:5][C:6](=[O:43])[C@H:7]([CH:40]([CH3:42])[CH3:41])[NH:8][C:9](=[O:39])[CH2:10][CH:11]1[CH2:17][CH2:16][C:15]([C@@H:18]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH3:19])=[CH:14][CH:13]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:12]1=[O:38].[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3](=[O:47])[C@H:4]([CH:44]([CH3:46])[CH3:45])[NH:5][C:6](=[O:43])[C@H:7]([CH:40]([CH3:41])[CH3:42])[NH:8][C:9](=[O:39])[CH2:10][CH:11]1[CH2:17][CH2:16][C:15]([C@@H:18]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH3:19])=[CH:14][CH:13]([CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:12]1[OH:38]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 677819852-(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-1-oxo-ethyl-valinyl-valine methyl ester

Product 1

HCID 700866982-(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-hydroxy-cyclohept-4-en-1-yl)-1-oxo-ethyl-valinyl-valine methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of the above (38) (0.47 g) in ethanol (15 mL) was added at room temperature NaBH4 (55 mg). After stirring for 30 min the reaction was carefully quenched with acetone then aqueous 1N HCl. The reaction was extracted with ethyl acetate, washed with saturated NaCl, dried over MgSO4 and evaporated. The product (39) was obtained as a mixture of isomers by flash chromatography on silica gel eluted with 50% CHCl3 in ethyl acetate (0.42 g, 89%). TLC Rf 0.36, 0.33 (97:3 CHCl3 :MeOH); MS DCl/NH3 (M+H)+ =650.4.

Workup

  1. customwas carefully quenched with acetone
  2. extractionThe reaction was extracted with ethyl acetate
  3. washwashed with saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-72d4386e6e9a48c29988ade4754fda43
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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