Sodium Hydroxide → HCID 59867777, compound

HRID 1662782Notes

Reaction equation

HRID 1662782 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[O:24][C:25]([F:28])([F:27])[F:26])(=[O:15])=[O:14])[C:8](=[O:29])[C:7]2([N:46]1[CH2:55][C@H:54]([OH:56])[CH2:53][C@H:47]1[C:48]([N:50]([CH3:52])[CH3:51])=[O:49])[C:30]1[CH:35]=[C:34]([CH:36](O)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:33]=[CH:32][C:31]=1[O:44][CH3:45].[OH-].[Na+]>C(O)(C(F)(F)F)=O.O>[CH2:36]([C:34]1[CH:33]=[CH:32][C:31]([O:44][CH3:45])=[C:30]([C:7]2([N:46]3[CH2:55][C@H:54]([OH:56])[CH2:53][C@H:47]3[C:48]([N:50]([CH3:52])[CH3:51])=[O:49])[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([Cl:3])[CH:5]=3)[N:9]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[O:24][C:25]([F:26])([F:27])[F:28])(=[O:15])=[O:14])[C:8]2=[O:29])[CH:35]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 59867770HCID 59867770, compound

Product 1

HCID 59867777HCID 59867777, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of 5 mg of NaBH4 in TFA (1 ml) was stirred for 15 minutes at room temperature, then, a solution of 28.1 mg of the compound obtained in Example 249 in TFA (3 ml) was added dropwise over 10 minutes. Two hours later, the solution was diluted with water, neutralized with NaOH, and the resulting mixture was extracted with CHCl3. The organic layer was washed with water and with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: MeOH/CHCl3=2/98; v/v) to obtain 25.3 mg of the title compound (colorless amorphous).

Workup

  1. extractionthe resulting mixture was extracted with CHCl3
  2. washThe organic layer was washed with water and with saturated brine
  3. dry with materialdried over MgSO4
  4. customthe drying agent was separated by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: MeOH/CHCl3=2/98; v/v)

Sources & evidence

ORD record
ord-27af87b788214ca0810c79a8abc723a8
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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