Water → HCID 71230933, compound

HRID 589516Notes

Reaction equation

HRID 589516 reaction equation
[C:1]([C:5]1[CH:37]=[CH:36][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[C:19]4[CH:26]=[C:25]([C:27]5[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH:28]=5)[NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[C:13]=2[CH2:34][OH:35])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].O>CO.C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[C:19]4[CH:26]=[C:25]([C:27]5[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH:28]=5)[NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[C:13]=2[CH2:34][OH:35])=[O:10])=[CH:36][CH:37]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 71231450HCID 71231450, compound

Product 1

HCID 71230933HCID 71230933, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of Intermediate 49 (80 mg, 0.162 mmol) in MeOH/DCM (1:1) were added cerium(III) chloride heptahydrate (66.3 mg, 0.178 mmol) and NaBH4 (6.1 mg, 0.162 mmol). The resulting mixture was stirred at r.t. for 2 hrs. Water was added, and the mixture was extracted three times with DCM/isopropanol (3:1). The combined organic layers were dried, filtered, and evaporated to dryness. The resulting residue was purified using flash chromatography (silica gel, EtOAc/MeOH/N H3 gradient) to yield Example 55.

Workup

  1. extractionthe mixture was extracted three times with DCM/isopropanol (3:1)
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting residue was purified
  6. customto yield Example 55

Sources & evidence

ORD record
ord-ed6c1b4d50994c9b8b3ff3dac097af95
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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