Water → HCID 58499611, compound

HRID 910270Notes

Reaction equation

HRID 910270 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([S:11]([NH:14][C@@H:15]([C:17]2[N:21]([CH2:22][CH3:23])[C:20]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N:31]4[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]4)[CH:26]=3)=[N:19][N:18]=2)[CH3:16])(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[Cl:10].O>CO>[Cl:3][C:4]1[CH:5]=[C:6]([S:11]([NH:14][C@@H:15]([C:17]2[N:21]([CH2:22][CH3:23])[C:20]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N:31]4[CH2:32][CH2:33][CH:34]([OH:37])[CH2:35][CH2:36]4)[CH:26]=3)=[N:19][N:18]=2)[CH3:16])(=[O:12])=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58499557HCID 58499557, compound

Product 1

HCID 58499611HCID 58499611, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (0.021 g) was added at 0° C. to a solution of the compound (0.150 g) of Example 8 in methanol (3.0 ml), and the mixture was stirred at room temperature for 16 hours. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over MgSO4, filtered, and evaporated under reduced pressure to remove the solvent. The resulting crude product was purified by column chromatography (neutral OH SiO2, methanol/chloroform=1/50 to 1/10) and then recrystallized (ethyl acetate-hexane) to give 0.113 g of the titled compound (Compound 93) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe resulting crude product was purified by column chromatography (neutral OH SiO2, methanol/chloroform=1/50 to 1/10)
  8. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0619cd2556f34541a7ee2063fb076518
Source dataset
uspto-grants-2011_09
Patent number
US08022091B2

Reaction notes

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