Sodium borohydride → HCID 58158143, compound

HRID 1916269Notes

Reaction equation

HRID 1916269 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][S:14][C:15]3[C:24]([C:25]#[N:26])=[C:23]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH2:34][C@@H:35]([OH:38])[CH2:36][OH:37])=[CH:29][CH:28]=4)[C:22]4[C:21](=[O:39])[CH2:20][CH2:19][CH2:18][C:17]=4[N:16]=3)[N:12]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][S:14][C:15]3[C:24]([C:25]#[N:26])=[C:23]([C:27]4[CH:28]=[CH:29][C:30]([O:33][CH2:34][C@@H:35]([OH:38])[CH2:36][OH:37])=[CH:31][CH:32]=4)[C:22]4[CH:21]([OH:39])[CH2:20][CH2:19][CH2:18][C:17]=4[N:16]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 58158151HCID 58158151, compound

Product 1

HCID 58158143HCID 58158143, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

25 mg (0.043 mmol) of the compound from Example 3 were initially charged in 1 ml of THF and 0.1 ml of methanol, 0.8 mg (0.022 mmol) of sodium borohydride was added with stirring and the mixture was stirred at RT for 16 h. The reaction solution was diluted with about 2 ml of water and purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% TFA).

Workup

  1. stirringthe mixture was stirred at RT for 16 h
  2. custompurified by preparative HPLC (Chromasil, water/acetonitrile+0.1% TFA)

Sources & evidence

ORD record
ord-099a9e4069f34919840a9bd747866fe1
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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