Sodium borohydride → [4-Hydroxymethyl-2-phenylbenzoyl]methionine methyl ester

HRID 2121125Notes

Reaction equation

HRID 2121125 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 105712674-Formyl-2-phenylbenzoyl methionine methyl ester

Product 1

HCID 20622833[4-Hydroxymethyl-2-phenylbenzoyl]methionine methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the resultant compound from Example 16E in ethanol at 0° C. is added sodium borohydride (0.5 equivalent), and the reaction is stirred at 0° C. until TLC analysis shows the reaction to be complete. The reaction mixture is extracted with ether, which is washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is then purified by column chromatography on silica gel to afford the title product.

Workup

  1. customthe reaction
  2. extractionThe reaction mixture is extracted with ether, which
  3. washis washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is then purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-baaa64d79a3245adaf5a54d6404f8fe7
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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