(1R,5S)-3-Oxabicyclo[3.2.0]heptane-2,4-dione → 2-{Benzyl-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexyl]carbamoyl}cyclobutanecarboxylic acid

HRID 1817748Notes

Reaction equation

HRID 1817748 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15][O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@@H:31]12[C:38](=[O:39])[O:37][C:35](=[O:36])[C@@H:32]1[CH2:33][CH2:34]2>>[CH2:1]([N:8]([CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15][O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])[CH2:10]1)[C:38]([CH:31]1[CH2:34][CH2:33][CH:32]1[C:35]([OH:37])=[O:36])=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 11400767(1R,5S)-3-Oxabicyclo[3.2.0]heptane-2,4-dioneHCID 57882734Benzyl-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexyl]amine

Product 1

HCID 115120882-{Benzyl-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexyl]carbamoyl}cyclobutanecarboxylic acid

Procedure

Analogous to the reaction conditions of example 1, benzyl-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexyl]amine and cis-cyclobutane-1,2-dicarboxylic anhydride give 2-{benzyl-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexyl]carbamoyl}cyclobutanecarboxylic acid. C32H38N2O5 (530.67), MS (ESI): 531 (MH+).

Sources & evidence

ORD record
ord-1c57d94f516f4978b7ce72eab62004ae
Source dataset
uspto-grants-2009_10
Patent number
US07598281B2

Reaction notes

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