2,6-Diisopropylphenyl isocyanate → 4-(2,4-Dioxo-1,3-diazaspiro[4.5]dec-1-yl)benzoic acid ethyl ester

HRID 1966954Notes

Reaction equation

C(C1C=CC=C(C(C)C)C=1N=[C:14]=[O:15])(C)C.[CH2:16]([O:18][C:19](=[O:36])[C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2([C:33](=[O:35])[NH2:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:22][CH:21]=1)[CH3:17]>C1(C)C=CC=CC=1>[CH2:16]([O:18][C:19](=[O:36])[C:20]1[CH:21]=[CH:22][C:23]([N:26]2[C:27]3([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:33](=[O:35])[NH:34][C:14]2=[O:15])=[CH:24][CH:25]=1)[CH3:17]

Participants

Conditions

Temperature: 180 °C

Procedure

380 μl (1.85 mmol, 1.2 eq.) of 2,6-diisopropylphenyl isocyanate are added to a solution of 450 mg (1.55 mmol, 1 eq.) of 4-(1-carbamoyl-cyclohexylamino)benzoic acid ethyl ester in 15 ml of toluene. The reaction medium is stirred at 180° C. for 2 hours with microwave irradiation. The toluene is evaporated off and the residue is purified on silica gel (heptane/ethyl acetate). The product 4-(2,4-dioxo-1,3-diazaspiro[4.5]dec-1-yl)benzoic acid ethyl ester is obtained in the form of a white solid.

Workup

customThe toluene is evaporated off
customthe residue is purified on silica gel (heptane/ethyl acetate)

Sources & evidence

ORD record: ord-b611f4d70b9748e1885d23bde8e9c63f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420682B2

Reaction notes

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