Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 55903

Reaction equation

HRID 55903 reaction equation
N(C(OC(C)(C)C)=O)[C@H](C(O)=[O:5])C.[CH:14]1([N:20]=[C:21]=[N:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>O1CCOCC1>[C:21]([NH:20][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)([NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:5]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

t-Boc-Ala (4.16 gr, 22 mmol) was dissolved in 11 ml dioxane. N,N′-Dicyclohexylcarbodiimide (DCC) (11 mmol in 11 ml 1 M DMF) was then added and the reaction was carried out for 3 hours at 25° C. under stirring. Dicyclohexylurea (DCU) formed was removed by centrifugation. The symmetrical anhydride product thus obtained (t-Boc-Ala-anhydride) was reacted overnight under stirring with 2-aminofluorene (0.925 g, 11 mmol) in 30 ml dioxane-water (1:1, v:v) containing 11 mmol of NaHCO3. The white solid formed was collected and dried under P2O5 in vacuum for 24 hours. Intermediate a was obtained in 60% yield (1.31 g, 3.34 mmol). It migrated on TLC (dichloromethane) with Rt=0.17. Mass-spectroscopy revealed a mass of 352.45 Da (calculated mass=352.2 Da).

Sources & evidence

ORD record
ord-326f8ed9aff5478a8f64bf07257cdb75
Source dataset
uspto-grants-2016_09
Patent number
US09433683B2

Linked notes

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