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

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

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 6344Dichloromethane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
特許番号
US05763437

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