Sodium borohydride → HCID 59232587, compound

HRID 2426984Notes

Reaction equation

HRID 2426984 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]([CH3:21])([CH3:20])[C:12]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[O:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C.C(Cl)Cl.C([O-])(O)=O.[Na+]>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:11]([CH3:20])([CH3:21])[C:12]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[O:13])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 59232656HCID 59232656, compound

Product 1

HCID 59232587HCID 59232587, compoundYield 89.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the title compound of Example 368 (20 mg, 0.053 mmol) in ethanol (1 ml) was added sodium borohydride (2 mg, 0.053 mmol) at ° C. The reaction mixture was stirred for 2 h. It was diluted with DCM and saturated aqueous NaHCO3. After separation, the organic extract was washed (brine), dried (MgSO4) and concentrated. The crude product was purified by silica gel flash chromatography using 0 to 50% ethyl acetate in heptane to afford the title compound of Example 371 as a white solid (18 mg, 89% yield). LC/MS (m/z) 381.19 [(M+1)+]; HPLC Rt: 3.246 min. 1H NMR (400 MHz, MeOD) δ ppm 7.36-7.40 (5H, m) 7.28-7.23 (4H, m) 7.20-7.16 (1H, m) 7.06 (1H, s) 4.79-4.75 (1H, m) 4.64 (1H, s) 1.4-1.39 (9H, m).

Workup

  1. customAfter separation
  2. extractionthe organic extract
  3. washwas washed (brine)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-1145322659d049d09eb67af1ad319b2c
Source dataset
uspto-grants-2011_06
Patent number
US07968577B2

Reaction notes

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