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Tetrahydrofuran → 2-Amino-4'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone

HRID 275849
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인쇄 미리보기

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HRID 275849 반응식
O1CCCC1.CN(OC)[C:8](=[O:17])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH2:16].[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([Li])CCC>C(OC(=O)C)C.O.CCCCCC>[NH2:16][C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([C:32]1[CH:31]=[CH:30][C:29]([CH2:28][NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[CH:34][CH:33]=1)=[O:17]
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참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 12453839tert-butyl N-[(4-bromophenyl)methyl]carbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

생성물 1

HCID 183153642-Amino-4'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone수율 25%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8058Hexane용매
HCID 8857Ethyl Acetate용매

실험 절차

A tetrahydrofuran (30 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (3.21 g) and N-tert-butoxycarbonyl-4-bromobenzylamine (2.86 g) was cooled to −78° C. To the solution kas gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (31 ml). To the mixture were then added water (100 ml) and acetic acid ethyl ester (100 ml). The organic layer was washed with water and dried over anhydrous MgSO4. The solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography. followed by crystallization. The crystals were collected to give 2-amino-4′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (0.9 g) as a pale yellow crystalline product.

후처리

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. distillationThe solvent was then distilled off
  4. customthe residue was purified by means of a silica gel column chromatography
  5. customfollowed by crystallization
  6. customThe crystals were collected

출처 및 근거

ORD 기록
ord-79d384d4b9734a568bbbe4fa09c91c97
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06352982B1

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