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Potassium Hydroxide → (1, 1-dimethyl-2-(4-oxo-5-(2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-ylmethyl)-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)-carbamic acid tert-butyl ester

HRID 398787
ノート
印刷プレビュー

反応式

HRID 398787 の反応式
[OH-].[K+].[C:3]([O:7][C:8](=[O:33])[NH:9][C:10]([CH3:32])([CH3:31])[CH2:11][C:12](=[O:30])[NH:13][CH:14]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][C:24]3[C:29]([C:17]=2[CH2:16][CH2:15]1)=[CH:28][CH:27]=[CH:26][CH:25]=3)([CH3:6])([CH3:5])[CH3:4].Br[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[C:48]2[N:52]([C:53]([C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[N:51]=[N:50][N:49]=2)=[CH:38][CH:37]=1.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C.O>[C:3]([O:7][C:8](=[O:33])[NH:9][C:10]([CH3:32])([CH3:31])[CH2:11][C:12](=[O:30])[NH:13][CH:14]1[C:20](=[O:21])[N:19]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:48]3[N:52]([C:53]([C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=4)([C:60]4[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=4)[C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[N:51]=[N:50][N:49]=3)=[CH:40][CH:41]=2)[C:18]2[CH:22]=[CH:23][C:24]3[C:29]([C:17]=2[CH2:16][CH2:15]1)=[CH:28][CH:27]=[CH:26][CH:25]=3)([CH3:6])([CH3:4])[CH3:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 53757316HCID 53757316、化合物

生成物 1

HCID 54197216(1, 1-dimethyl-2-(4-oxo-5-(2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-ylmethyl)-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)-carbamic acid tert-butyl ester
収率 49.9%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of dry powdered potassium hydroxide (0.23 g, 4.0 mmol) and (1,1-dimethyl-2-(4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)carbamic acid tert-butyl ester (0.49 g, 1.0 mmol) in DMSO (15 ml) was stirred for 0.5 h under an atmosphere of nitrogen. 5-(4'-Bromomethyl-biphenyl-2-yl)-N-(triphenylmethyl)tetrazole (0.59 g, 1.1 mmol) was added and the mixture was stirred for 1 h. A 10% aqueous solution of ammoniumchloride (30 ml), water (100 ml) and ethyl acetate (60 ml) were added and the phases were separated. The organic layer was dried (MgSO4), and the solvent was evaporated in vacuo. Purification by columm chromatography on silica gel (100 g) using heptane and ethyl acetate (2:3) as eluent afforded 0.45 g of (1, 1-dimethyl-2-(4-oxo-5-(2'-(N -triphenylmethyltetrazol-5-yl)biphenyl-4-ylmethyl)-2,3,4,5-tetrahydro- 1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)- carbamic acid tert-butyl ester.

後処理

  1. customthe phases were separated
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent was evaporated in vacuo
  4. customPurification by columm chromatography on silica gel (100 g)

出典と根拠

ORDレコード
ord-4869f446593941db911bb109f2058444
出典データセット
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05817654

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート