Benzyl Alcohol → HCID 70945575, compound

HRID 2362433Notes

Reaction equation

HRID 2362433 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:29])([CH:12]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[C:9]([OH:11])=[O:10])[CH:5]=[N:6][CH:7]=1.[CH2:30]([OH:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([N:40]([CH2:43]C)CC)C.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:46]C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:9]([O-:11])(=[O:10])[CH3:8].[NH4+:6].[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:40][C:43](=[O:46])[O:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([CH3:29])[CH:12]([O:21][Si:22]([C:25]([CH3:27])([CH3:26])[CH3:28])([CH3:24])[CH3:23])[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 69083222HCID 69083222, compound

Product 2

HCID 517165Ammonium AcetateHCID 70945575HCID 70945575, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To crude 2-(5-bromopyridin-3-yl)-3-(tert-butyldimethylsilyloxy)-3-(2,5-difluorophenyl)-2-methylpropanoic acid (450 mg, 0.925 mmol) in toluene (12 mL) was added benzyl alcohol (0.096 mL, 0.925 mmol), triethylamine (0.258 mL, 1.850 mmol) and diphenyl phosphorazidate (0.200 mL, 0.925 mmol). The mixture was placed in a heat bath set to 60° C. for 18 h, concentrated and purified via preparative liquid chromatography (Sunfire C18 OBD 30×100 mm 5 μm, A=95% H2O/5% Acetonitrile, B=95% Acetonitrile/5% H2O, Modifier 10 mM Ammonium Acetate, 0.00 min=0% B, 8.0 min=100% B, 13.0 min=100% B, Flow rate=40 mL/min) providing 80 mg (15%) benzyl 2-(5-bromopyridin-3-yl)-1-(tert-butyldimethylsilyloxy)-1-(2,5-difluorophenyl)propan-2-ylcarbamate. Mass Spectral Anal. Calcd. for [M+H]+ C28H33BrF2N2O2Si: 591.1. found 590.0.

Workup

  1. customThe mixture was placed in a heat bath
  2. concentrationconcentrated
  3. custompurified via preparative liquid chromatography (Sunfire C18 OBD 30×100 mm 5 μm

Sources & evidence

ORD record
ord-fd2f2796691641b9af56fe5f847ec562
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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