Sodium borohydride → HCID 21729191, compound

HRID 1957396Notes

Reaction equation

HRID 1957396 reaction equation
[Cl:1][CH2:2]C(CCl)=O.[C:7]([NH:17][C@H:18]([C:23]([OH:25])=O)[CH2:19][CH:20]([CH3:22])[CH3:21])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[BH4-].[Na+]>CO>[CH2:19]([C@H:18]([NH:17][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])[C@H:23]([OH:25])[CH2:2][Cl:1])[CH:20]([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 88326106HCID 88326106, compound

Product 1

HCID 21729191HCID 21729191, compoundYield 117.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-Cbz-leucine chloromethyl ketone (2.0 g) in 20 mL of methanol was added, at 0° C., 1.0 g of sodium borohydride and the mixture was stirred at ambient temperature for 24 h. The solution was concentrated under reduced pressure and the residue partitioned between 20 mL of saturated aqueous NH4Cl and 500 ml of diethyl ether. The organic fraction was separated, dried over MgSO4 and concentrated in vacuo and the residue purified by silica gel chromatography to yield 1.8 g of white solid.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue partitioned between 20 mL of saturated aqueous NH4Cl and 500 ml of diethyl ether
  3. customThe organic fraction was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-56773197f00f4d0a889319d10df6fd53
Source dataset
uspto-grants-1998_07
Patent number
US05783701

Reaction notes

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