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

HRID 1831013노트

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HRID 1831013 반응식
[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]

참가 물질

5

반응물 4

HCID 6342Acetonitrile2회HCID 11430Potassium CarbonateHCID 9965968Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoateHCID 154871552'-(Bromomethyl)[1,1'-biphenyl]-4-carbonitrile

생성물 1

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

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온도
82.5 °C

실험 절차

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].

후처리

  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]

출처 및 근거

ORD 기록
ord-3476f512d8cb451990d00c11912af97f
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067546B2

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