Triethylamine → tert-Butyl 4-(N-tertiary-butyloxycarbonyl-N-methylamino)cinnamate

HRID 412479노트

반응식

HRID 412479 반응식
[C:1]([O:5][C:6]([N:8]([CH3:16])[C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:1]([O:5][C:6]([N:8]([C:9]1[CH:14]=[CH:13][C:12]([CH:19]=[CH:18][C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:11][CH:10]=1)[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 18537740N-Boc 4-Iodo-N-methylaniline

생성물 1

HCID 57300103tert-Butyl 4-(N-tertiary-butyloxycarbonyl-N-methylamino)cinnamate수율 67.2%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of N-tertiary-butyloxycarbonyl-N-methyl4-iodoaniline (11 g, Reference Example 9), tert-butyl acrylate (8.4 g), tris-(o-tolyl)phosphine (500 mg), palladium (II) acetate (150 mg), and triethylamine (7 g) in DMF (20 mL) was stirred at 90° C. under nitrogen overnight. The reaction mixture was cooled to room temperature then partitioned between ethyl acetate (500 mL) and hydrochloric acid solution (500 mL, 1M). The organic phase was dried and then evaporated. The residue was crystallised from cyclohexane to give the title compound (7.4 g) as a white solid.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthen partitioned between ethyl acetate (500 mL) and hydrochloric acid solution (500 mL, 1M)
  3. customThe organic phase was dried
  4. customevaporated
  5. customThe residue was crystallised from cyclohexane

출처 및 근거

ORD 기록
ord-e14dbb123eba43899eb525843e93150e
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562851B2

반응 노트

불러오는 중…