Triethylamine → Methyl 4-((tert-butoxycarbonyl)amino)-2,6-dichlorobenzoate

HRID 449869노트

반응식

HRID 449869 반응식
FC(F)(F)S(O[C:7]1[C:12]([Cl:13])=[CH:11][C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][C:8]=1[Cl:22])(=O)=O.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>CO.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:18]([O:17][C:15]([NH:14][C:10]1[CH:11]=[C:12]([Cl:13])[C:7]([C:15]([O:17][CH3:18])=[O:16])=[C:8]([Cl:22])[CH:9]=1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 206100814-(Tert-butoxycarbonylamino)-2,6-dichlorophenyl trifluoromethanesulfonate

생성물 1

HCID 20610066Methyl 4-((tert-butoxycarbonyl)amino)-2,6-dichlorobenzoate수율 119.4%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(tert-butoxycarbonylamino)-2,6-dichlorophenyl trifluoromethanesulfonate (14 g, 34 mmol), dppp (1.4 g, 3.4 mmol), Pd(OAc)2 (0.84 g, 3.4 mol) and Et3N (19.6 mL) in MeOH (112 mL) and DMF (224 mL) was refluxed under an atmosphere of carbon monoxide (10 atm) overnight. The reaction was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (petroleum ether/EtOAc 80:1) to give methyl 4-(tert-butoxy carbonylamino)-2,6-dichlorobenzoate (6.5 g, yield: 60%). 1H NMR (CDCl3, 400 MHz) δ 7.40 (s, 2H), 6.56 (brs, 1H), 3.94 (s, 3H), 1.51 (s, 9H).

후처리

  1. temperaturewas refluxed under an atmosphere of carbon monoxide (10 atm) overnight
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (petroleum ether/EtOAc 80:1)

출처 및 근거

ORD 기록
ord-119c8373af7844c090a699bc5e9cf13f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486950B2

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