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

HRID 412479ノート

反応式

HRID 412479 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 80271Tri-o-tolylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e14dbb123eba43899eb525843e93150e
出典データセット
uspto-grants-2003_05
特許番号
US06562851B2

反応ノート

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