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

HRID 2264098Notes

Reaction equation

HRID 2264098 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-1ac1da8a985c48f6b56539afcbf5e1a2
Source dataset
uspto-grants-2010_12
Patent number
US07850947B2

Reaction notes

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