1-Aminocyclohexanecarboxylic acid → Fmoc-aminocyclohexane carboxylic acid

HRID 478616Notes

Reaction equation

HRID 478616 reaction equation
[NH2:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:11](Cl)([O:13][CH2:14][CH:15]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12].C(N(C(C)C)CC)(C)C.[OH-].[Na+]>O1CCOCC1.C(Cl)Cl.CO>[C:11]([CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1([NH2:1])[C:8]([OH:10])=[O:9])([O:13][CH2:14][CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:12]

Participants

7

Reactant 4

HCID 13661-Aminocyclohexanecarboxylic acidHCID 14798Sodium HydroxideHCID 343679-Fluorenylmethyl chloroformateHCID 81531Diisopropylethylamine

Product 1

HCID 56923993Fmoc-aminocyclohexane carboxylic acid

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound is prepared from 1-aminocyclohexane carboxylic acid (700 mmol), FMOC-chloride (770 mmol), Diisopropyl-ethylamine (770 mmol) and 770 ml NaOH 1N in 950 ml dioxan by conventional methods. Mp. 180-182° C.; Rf=0.21 (CH2Cl2/MeOH=95:5)

Sources & evidence

ORD record
ord-648137042f9245d091c8a8649c76bb05
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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