Triethylamine → 2-[3-(5-Methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexylcarbamoyl]cyclobutanecarboxylic acid

HRID 1817747Notes

Reaction equation

HRID 1817747 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([NH2:23])[CH2:18]1.C(N(CC)CC)C.[C@@H:31]12[C:38](=[O:39])[O:37][C:35](=[O:36])[C@@H:32]1[CH2:33][CH2:34]2>CN(C=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([NH:23][C:38]([CH:31]2[CH2:34][CH2:33][CH:32]2[C:35]([OH:37])=[O:36])=[O:39])[CH2:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11400767(1R,5S)-3-Oxabicyclo[3.2.0]heptane-2,4-dioneHCID 578827323-(5-Methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexylamine

Product 1

HCID 115612572-[3-(5-Methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexylcarbamoyl]cyclobutanecarboxylic acidYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg of 3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexylamine were dissolved in 0.97 ml of DMF, and 32 mg of triethylamine were added. 22 mg of cis-cyclobutane-1,2-dicarboxylic anhydride were then added, and the solution was stirred at RT overnight. The solution was purified directly by HPLC, which gave 36 mg of 2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxymethyl)cyclohexylcarbamoyl]cyclobutanecarboxylic acid. C25H32N2O5 (440.54), MS (ESI): 441 (MH+).

Workup

  1. customThe solution was purified directly by HPLC, which

Sources & evidence

ORD record
ord-25f5765f53b54b11bd1a44cb11691c36
Source dataset
uspto-grants-2009_10
Patent number
US07598281B2

Reaction notes

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