Triethylamine → 3-(2-tert-Butoxycarbonylamino-2-methylpropyl)benzoic acid methyl ester

HRID 1866508노트

반응식

HRID 1866508 반응식
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]([CH3:18])([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C]=O>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:5][C:6](=[O:19])[C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:19])([CH3:18])[CH3:17])[CH:11]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 58907464tert-butyl N-[1-(3-bromophenyl)-2-methylpropan-2-yl]carbamateHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 597135613-(2-tert-Butoxycarbonylamino-2-methylpropyl)benzoic acid methyl ester수율 116.5%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 887Methanol용매

실험 절차

A solution of [2-(3-bromophenyl)-1,1-dimethylethyl]carbamic acid tert-butyl ester (Preparation 32) (7.0 g, 21 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.74 g, 2.1 mmol) and triethylamine (5.94 ml, 43 mmol) in methanol (250 ml) was heated to 100° C. under 100 psi carbon monoxide for 12 hours. The reaction mixture was filtered through arbocel and the filtrate concentrated in vacuo and purified by flash column chromatography on silica gel eluting with dichloromethane:pentane (50:50 by volume) to afford the title compound as a yellow solid (3.76 g). 1H NMR (400 MHz, CDCl3) δ=7.92-7.90 (1H, m), 7.82 (1H, s), 7.35-7.34 (2H, m), 4.24 (1H, bs), 3.90 (3H, s), 3.05 (2H, s), 1.48 (9H, s), 1.26 (6H, s). LRMS (electrospray) m/z 208 [M+H−BOC]+

후처리

  1. filtrationThe reaction mixture was filtered through arbocel
  2. concentrationthe filtrate concentrated in vacuo
  3. custompurified by flash column chromatography on silica gel eluting with dichloromethane:pentane (50:50 by volume)

출처 및 근거

ORD 기록
ord-df2fb9691c814956ac4f62187dde65ab
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629358B2

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