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

HRID 449869ノート

反応式

HRID 449869 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-119c8373af7844c090a699bc5e9cf13f
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

反応ノート

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