Trimethylsilyldiazomethane → HCID 86617422, compound

HRID 2076672Notes

Reaction equation

HRID 2076672 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([O:12][C:13]([C:15]1[C:39]([OH:40])=[C:38]([C:41]([F:44])([F:43])[F:42])[CH:37]=[CH:36][C:16]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[C:27]([Cl:35])[CH:26]=2)=[CH:21][CH:20]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>C1(CO)C=CC=CC=1>[Cl:35][C:27]1[CH:26]=[C:25]([C:22]2[CH:21]=[CH:20][C:19]([O:18][CH2:17][C:16]3[C:15]([C:13]([O:12][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:14])=[C:39]([OH:40])[C:38]([C:41]([F:44])([F:42])[F:43])=[CH:37][CH:36]=3)=[CH:24][CH:23]=2)[CH:30]=[CH:29][C:28]=1[CH2:31][C:32]([O:34][CH3:1])=[O:33]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 11649520HCID 11649520, compound

Product 1

HCID 86617422HCID 86617422, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Procedure

A trimethylsilyldiazomethane-0.6M hexane solution (0.20 ml, 0.12 mmol) was added to a solution of (4′-{[2-(tert-butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-3-chloro-1,1′-biphenyl-4-yl)acetic acid (60 mg, 0.11 mmol) obtained in Example (18-4) in a mixture of benzene-methanol (4:1, 2.5 ml), and the mixture was stirred for 1 hour. The residue obtained by removing the solvent under reduced pressure was purified by silica gel preparative thin layer chromatography (developing solvent: hexane/methylene chloride/ethyl acetate=9/1/1) to give the title compound (45 mg, yield: 73%).

Workup

  1. customThe residue obtained
  2. customby removing the solvent under reduced pressure
  3. customwas purified by silica gel preparative thin layer chromatography (developing solvent: hexane/methylene chloride/ethyl acetate=9/1/1)

Sources & evidence

ORD record
ord-98167909f58549d3b5b234b3be4fa0fc
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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