Benzyl Alcohol → HCID 59136101, compound

HRID 504926Notes

Reaction equation

HRID 504926 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. melting point 160° C.

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-f8e045f9e6594a299d6f24559c2ec1f0
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

Loading…