Ethyl Acetate → N,N'-Dicyclohexylurea

HRID 2250311Notes

Reaction equation

HRID 2250311 reaction equation
C([O:5]C(NOCC(O)=O)=O)(C)(C)C.C(OCC)(=O)C.[CH:20]1([N:26]=[C:27]=[N:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.ON1C(=O)CCC1=O>C(#N)C>[CH:29]1([NH:28][C:27]([NH:26][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[O:5])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2755974(Boc-aminooxy)acetic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyloxycarbonylaminoxy acetic acid was dissolved in ice-cooled ethyl acetate or acetonitrile and treated with N,N′-dicyclohexylcarbodiimide (1.0 equivalent) and N-hydroxysuccinimide (1.0 equivalent). The reaction mixture was stirred at room temperature overnight. The N,N′-dicyclohexylurea formed was removed by filtration and the filtrate was evaporated to dryness in vacuo. The crude Boc-AOA-OSu was either used directly in the next step or purified by recrystallisation from chloroform. Adopted from Kurth et al. J. Med. Chem. 1993, 36, 1255.

Sources & evidence

ORD record
ord-aa3c5d6c3ee7456b988e1514de59ee6f
Source dataset
uspto-grants-2008_01
Patent number
US07316999B2

Reaction notes

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