Lithium Chloride → HCID 59536918, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][CH:25]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])[CH2:26][C:27](OC)=[O:28])=[O:23])[N:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[Li+].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>COCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:17])([F:18])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][CH:25]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])[CH2:26][CH2:27][OH:28])=[O:23])[N:9]=2)=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
Of the compound from Example 93A, 39 mg (0.07 mmol) were dissolved in 2 ml of 1,2-dimethoxyethane and admixed at room temperature in succession with 4.1 mg (0.11 mmol) of sodium borohydride and with 0.6 mg (0.014 mmol) of lithium chloride. Subsequently the mixture was stirred at 85° C. for 16 h. For work-up, 10 ml of saturated aqueous sodium potassium tartrate solution were added and the mixture was extracted with three times 10 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated on a rotary evaporator. The crude product was purified by preparative HPLC [Method 19]. This gave 19 mg (49% of theory) of the target compound.
Workup
- extractionthe mixture was extracted with three times 10 ml of ethyl acetate
- dry with materialThe combined organic phases were dried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated on a rotary evaporator
- customThe crude product was purified by preparative HPLC [Method 19]
Sources & evidence
- ORD record
- ord-e1045594b64e4ca283326d583d961351
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796324B2
Reaction notes
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