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

HRID 919048노트

반응식

HRID 919048 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-35b3624a484f46eabe09acaf946b7d04
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09272990B2

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