Benzyl Alcohol → HCID 59136101, compound

HRID 1960548Notes

Reaction equation

HRID 1960548 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N:11]([CH3:20])[S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:10]=1)[NH:7][C:6]([C:21]1[S:22][CH:23]([CH2:26]C(O)=O)[CH2:24][N:25]=1)=[CH:5]2.[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.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:52])C=CC=CC=1>CN(C)C=O.O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N:11]([CH3:20])[S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:10]=1)[NH:7][C:6]([C:21]1[S:22][CH:23]([CH2:26][NH:40][C:43](=[O:52])[O:37][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:24][N:25]=1)=[CH:5]2

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59135922HCID 59135922, compound

Product 1

HCID 59136101HCID 59136101, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (2-{5-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (500 mg), benzyl alcohol (570 μL) and triethylamine (185 μL) in N,N-dimethylformamide (10 mL) was added diphenylphosphorylazide (287 μL) at room temperature, and the mixture was stirred under heating at 100° C. for 30 min. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (112 mg, yield 18%) as pale-yellow crystals from a fraction eluted with ethyl acetate:hexane=25:75.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-85cd7d5ed32a4ce18e3208ca08d4e573
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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