Acetonitrile → Methyl 2-[N-(tert-Butoxycarbonyl)-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate

HRID 1831013ノート

反応式

HRID 1831013 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:37]=[CH:36][C:33]([C:34]#N)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C(#[N:46])C>>[C:1]([O:5][C:6]([N:8]([C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[CH2:34][C:33]1[CH:36]=[CH:37][C:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]#[N:46])=[CH:31][CH:32]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 4

HCID 6342Acetonitrile2 回HCID 11430Potassium CarbonateHCID 9965968Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoateHCID 154871552'-(Bromomethyl)[1,1'-biphenyl]-4-carbonitrile

生成物 1

HCID 10874596Methyl 2-[N-(tert-Butoxycarbonyl)-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate

反応条件

温度
82.5 °C

実験手順

Methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN] obtained in Reference Example 3 (354 kg), a solution of 4-(2-bromomethylphenyl)benzonitrile [BMB] in acetonitrile obtained in Reference Example 4 (1), and anhydrous potassium carbonate (475 kg) were added to acetonitrile (1600 kg), and the mixture was heated (80 to 85° C.) under reflux for about 5 hours. The reaction solution was cooled, and the insoluble were separated and washed with acetonitrile (320 kg). The filtrated washing was concentrated under reduced pressure to give concentrate of methyl 2-[N-t-butoxycarbonyl-N-[(2′-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].

後処理

  1. temperatureunder reflux for about 5 hours
  2. temperatureThe reaction solution was cooled
  3. customthe insoluble were separated
  4. washwashed with acetonitrile (320 kg)
  5. washThe filtrated washing
  6. concentrationwas concentrated under reduced pressure
  7. customto give
  8. concentrationconcentrate of methyl 2-[N-t-butoxycarbonyl-N-[(2′-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN]

出典と根拠

ORDレコード
ord-3476f512d8cb451990d00c11912af97f
出典データセット
uspto-grants-2006_06
特許番号
US07067546B2

反応ノート

読み込み中…