Sodium borohydride → HCID 67348945, compound

HRID 1916338Notes

Reaction equation

HRID 1916338 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]3[S:15][CH2:14][C:13](=[O:16])[NH:12][C:11]=3[CH:17]=2)[CH2:5][C@@H:4]([CH2:18][CH2:19][CH2:20][NH:21][C@H:22]2[C:32]3[C:33]4[N:24]([C:25](=[O:34])[CH:26]=[N:27][C:28]=4[CH:29]=[CH:30][CH:31]=3)[CH2:23]2)[O:3]1.[BH4-].[Na+]>CO.ClCCCl>[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]3[S:15][CH2:14][C:13](=[O:16])[NH:12][C:11]=3[CH:17]=2)[CH2:5][C@@H:4]([CH2:18][CH2:19][CH2:20][NH:21][C@H:22]2[C:32]3[C:33]4[N:24]([C:25](=[O:34])[CH2:26][NH:27][C:28]=4[CH:29]=[CH:30][CH:31]=3)[CH2:23]2)[O:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 45380794HCID 45380794, compound

Product 1

HCID 67348945HCID 67348945, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 22134543HCID 22134543, compoundSolvent

Procedure

A solution of the compound of Example 48 (33 mg) in MeOH/DCE (5 mL; 4:1) was treated with NaBH4 (3 mg) for 30 min then quenched with 1M. HCl (1 mL) and partitioned between DCM and an aq. NH4OH solution. The org. layer was washed with water and brine, dried over MgSO4 and purified by CC (EA/MeOH 19:1 to 9:1 containing 1% NH4OH) affording a colourless solid (26 mg; 78% yield).

Workup

  1. customthen quenched with 1M
  2. customHCl (1 mL) and partitioned between DCM
  3. washlayer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. custompurified by CC (EA/MeOH 19:1 to 9:1 containing 1% NH4OH)
  6. customaffording a colourless solid (26 mg; 78% yield)

Sources & evidence

ORD record
ord-d5d8a1cadd864919a89e07b583a1d38c
Source dataset
uspto-grants-2013_12
Patent number
US08618092B2

Reaction notes

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