Sodium borohydride → HCID 9863133, compound

HRID 1358257Notes

Reaction equation

HRID 1358257 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([NH:12][C:13]([NH:15][C:16]2[CH:25]=[CH:24][C:23]3[C:22](=[O:26])[CH2:21][CH2:20][CH2:19][C:18]=3[CH:17]=2)=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.[BH4-].[Na+]>CO>[OH:26][CH:22]1[CH2:21][CH2:20][CH2:19][C:18]2[CH:17]=[C:16]([NH:15][C:13]([NH:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][N:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)=[O:14])[CH:25]=[CH:24][C:23]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 9884611HCID 9884611, compound

Product 1

HCID 9863133HCID 9863133, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of EXAMPLE 3 (0.093 g) in methanol (100 ml) was treated with sodium borohydride (0.3 g) and the mixture stirred overnight. Solvent was removed at reduced pressure the residue dissolved in ethyl acetate and washed with water and brine. The organic phase was dried (Na2SO4) solvent removed at reduced pressure and the residue triturated with diethyl ether to give the title compound (0.06 g) as a colourless solid. 1H NMR δ: 1.69 (2H, m), 1.87 (2H, m), 2.63 (3H, s), 2.67 (2H, m), 4.53 (1H, m), 5.01 (1H, d), 7.23-7.35 (3H, m), 7.79 (1H, dd), 8.29 (1H, dd), 8.36 (1H, s), 8.89 (1H, m), 9.90 (1H, s), 9.93 (1H, s). m/z (API+): 349 (MH+).

Workup

  1. customSolvent was removed at reduced pressure the residue
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried (Na2SO4) solvent
  5. customremoved at reduced pressure
  6. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-a2749ac703434fa993c9f6a3a2a3e230
Source dataset
uspto-grants-2003_07
Patent number
US06596730B1

Reaction notes

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