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N-tert-Butoxycarbonyl-L-tryptophan → (3S)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one

HRID 963465
ノート
印刷プレビュー

反応式

HRID 963465 の反応式
C(OC(N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1)=O)(C)(C)C.[NH2:23][CH:24]1[N:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[C:28]2[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=2[N:26]([CH2:42][C:43]([N:45]2[CH2:51][CH:50]3[CH2:52][CH2:53][CH:47]([CH2:48][CH2:49]3)[CH2:46]2)=[O:44])[C:25]1=[O:54]>C(#N)C.C(Cl)Cl>[NH2:23][C@H:24]1[N:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[C:28]2[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=2[N:26]([CH2:42][C:43]([N:45]2[CH2:51][CH:50]3[CH2:52][CH2:53][CH:47]([CH2:48][CH2:49]3)[CH2:46]2)=[O:44])[C:25]1=[O:54]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 19081160(3RS)-1-{(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl}-3-amino-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

生成物 1

HCID 54425021(3S)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one収率 46%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

To a solution of N-tert-butoxycarbonyl-L-tryptophan (0.70 g) in acetonitrile (20 ml) was added dropwise a solution of (3RS)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (1.00 g) in methylene chloride (5 ml) under stirring at ambient temperature. The mixture was stirred overnight. The precipitate was collected by filtration and the colorless solid was partitioned between methylene chloride and 0.5N NaOH. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford (3S)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (0.46 g) as s colorless crystal.

後処理

  1. stirringThe mixture was stirred overnight
  2. filtrationThe precipitate was collected by filtration
  3. customthe colorless solid was partitioned between methylene chloride and 0.5N NaOH
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b138eac3035940ed844fdebad43ac9a4
出典データセット
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05763437

反応ノート

読み込み中…

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