Sodium borohydride → HCID 23001281, compound

HRID 397999Notes

Reaction equation

HRID 397999 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:22])[CH2:10][S:11][C:12]2[NH:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][N:13]=2)=[CH:5][C:4]=1[F:23])#[N:2].[BH4-].[Na+]>CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:22])[CH2:10][S:11][C:12]2[NH:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][N:13]=2)=[CH:5][C:4]=1[F:23])#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23001294HCID 23001294, compound

Product 1

HCID 23001281HCID 23001281, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Step G (3.00 g, 9.00 mmol) was suspended in methanol (20 mL). Sodium borohydride (340 mg, 9.00 mmol) was added in portions at 0° C., and the suspension was stirred until it became homogeneous (1 hour). The reaction was quenched by the addition of saturated aqueous ammonium chloride until hydrogen evolution ceased. The resulting suspension was concentrated in vacuo and then partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title product as an off-white solid which was sufficiently pure for use in the next step.

Workup

  1. custom(1 hour)
  2. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride until hydrogen evolution
  3. concentrationThe resulting suspension was concentrated in vacuo
  4. custompartitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (50 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afdd5ad2840c4a7297954fae0cf60751
Source dataset
uspto-grants-2003_08
Patent number
US06610722B2

Reaction notes

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