Triethylamine → [5-(4-Bromo-phenyl)-oxazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester

HRID 919048Notes

Reaction equation

HRID 919048 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2C(O)=O)=[CH:4][CH:3]=1.[C:16]1([C@H:22]([OH:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([N:27]([CH2:30]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1>C1(C)C=CC=CC=1>[C:16]1([C@H:22]([O:24][C:30](=[O:39])[NH:27][C:9]2[N:10]=[CH:11][O:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6375161-Phenylethanol, (R)-HCID 616374135-(4-Bromophenyl)oxazole-4-carboxylic acid

Product 1

HCID 67963772[5-(4-Bromo-phenyl)-oxazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

5-(4-Bromo-phenyl)-oxazole-4-carboxylic acid (0.5 g, 1.9 mmol), (R)-1-phenyl-ethanol (0.25 mL, 2.0 mmol) and triethylamine (0.55 mL, 3.8 mmol) were dissolved in toluene (10 mL). Diphenylphosphoryl azide (0.5 mL, 2.3 mmol) was added and the reaction was heated to 80° C. The reaction was monitored by analytical LCMS and when complete was cooled and submitted to standard aqueous workup. The crude material was purified on silica gel to provide the title compound.

Workup

  1. temperaturecomplete was cooled
  2. customThe crude material was purified on silica gel

Sources & evidence

ORD record
ord-35b3624a484f46eabe09acaf946b7d04
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

Loading…