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4-Amino-3-chlorobenzoic acid → 3-chloro-4-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetamido]benzoic acid

HRID 2264098
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HRID 2264098 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11].C(N(C(C)C)C(C)C)C.[C:21]([NH:38][CH2:39][C:40](Cl)=[O:41])([O:23][CH2:24][CH:25]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22]>C1COCC1.C(Cl)Cl.C1COCC1>[CH:27]1[C:26]2[CH:25]([CH2:24][O:23][C:21]([NH:38][CH2:39][C:40]([NH:1][C:2]3[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=3[Cl:11])=[O:41])=[O:22])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]=2[CH:30]=[CH:29][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 172114-Amino-3-chlorobenzoic acidHCID 81531DiisopropylethylamineHCID 11758879Fmoc-Gly-Cl

생성물 1

HCID 669661463-chloro-4-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetamido]benzoic acid수율 75%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 21919333
Tetrahydrofurane dichloromethane
용매

실험 절차

A solution of 4-amino-3-chlorobenzoic acid (1.5 g; 8.75 mmol) and N-ethyldiisopropylamine (1.46 mL 8.75 mmol) in THF (50 mL) was added dropwise to a solution of Fmoc-glycylchloride (2.76 g; 8.75 mmol) in CH2Cl2/THF 1:1 (30 mL) and stirred at room temperature under N2. After 3 h the solvent was evaporated under vacuum. The residue was taken up with 0.5N HCl (50 mL), filtered and dried. The white solid was suspended in MeOH (30 mL) and stirred for 1 h, then was filtered and dried to give 4-[[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]acetyl]amino-3-chlorobenzoic acid (2.95 g; 6.5 mmol). Yield 75%.

후처리

  1. customAfter 3 h the solvent was evaporated under vacuum
  2. filtrationfiltered
  3. customdried
  4. stirringstirred for 1 h
  5. filtrationwas filtered
  6. customdried

출처 및 근거

ORD 기록
ord-1ac1da8a985c48f6b56539afcbf5e1a2
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07850947B2

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