Sodium borohydride → HCID 67350902, compound

HRID 527983Notes

Reaction equation

HRID 527983 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6](=[O:12])[N:5]3[CH2:13][C@@H:14]([NH:15][CH2:16][CH2:17][CH2:18][C@@H:19]4[O:23][C:22](=[O:24])[N:21]([C:25]5[CH:26]=[CH:27][C:28]6[S:33][CH2:32][C:31](=[O:34])[NH:30][C:29]=6[CH:35]=5)[CH2:20]4)[C:3]=1[C:4]=23.[BH4-].[Na+]>C(Cl)Cl.CO>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][CH2:7][C:6](=[O:12])[N:5]3[CH2:13][C@@H:14]([NH:15][CH2:16][CH2:17][CH2:18][C@@H:19]4[O:23][C:22](=[O:24])[N:21]([C:25]5[CH:26]=[CH:27][C:28]6[S:33][CH2:32][C:31](=[O:34])[NH:30][C:29]=6[CH:35]=5)[CH2:20]4)[C:3]=1[C:4]=23

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67352033HCID 67352033, compound

Product 1

HCID 67350902HCID 67350902, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of the compound of Example 79 (42 mg) in DCM/MeOH (2:1; 6 mL) was treated with NaBH4 (3.2 mg). After 30 min stirring at rt, the reaction mixture was quenched with 1M HCl (1 mL) and partitioned between DCM and aq. NH4OH. The org. layer was washed with water, dried over MgSO4, concentrated under reduced pressure and purified by CC (EA/MeOH 19:1 to 9:1), affording a beige solid (29 mg; 69% yield).

Workup

  1. customthe reaction mixture was quenched with 1M HCl (1 mL)
  2. custompartitioned between DCM and aq. NH4OH
  3. washlayer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by CC (EA/MeOH 19:1 to 9:1)
  7. customaffording a beige solid (29 mg; 69% yield)

Sources & evidence

ORD record
ord-cbd0b01ba9a94fe5b2d016d400cfe4f5
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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