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

HRID 1817744Notes

Reaction equation

HRID 1817744 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](=[O:12])([O-])[O-:10].[K+].[K+].Cl.NC1CCCC(C(OC)=[O:24])C1.C(N(CC1C=CC=CC=1)C1CCCC(C(OC)=O)C1)C1C=CC=CC=1.C([N:59]([CH2:76][C:77]1[CH:82]=[CH:81][CH:80]=CC=1)[CH:60]1[CH2:65][CH2:64][CH2:63][CH:62]([C:66]([O:68][CH2:69][C:70]2[CH:75]=[CH:74]C=CC=2)=O)[CH2:61]1)C1C=CC=CC=1.C[N:84]([CH:86]=[O:87])C>CC(OC)(C)C.O>[CH3:74][C:75]1[O:87][C:86]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=2)=[N:84][C:70]=1[CH2:69][O:68][CH2:66][CH:62]1[CH2:63][CH2:64][CH2:65][CH:60]([NH:59][C:76]([CH:77]2[CH2:82][CH2:81][CH:80]2[C:9]([OH:10])=[O:12])=[O:24])[CH2:61]1

Participants

9

Reactant 6

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13216967Methyl 3-aminocyclohexane-1-carboxylate hydrochlorideHCID 57882728Methyl 3-dibenzylaminocyclohexanoateHCID 57882731Benzyl 3-dibenzylaminocyclohexanoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

At room temperature, 28.7 g of benzyl bromide and then 37 g of potassium carbonate were added to a suspension of 9.37 g of methyl 3-aminocyclohexanecarboxylate hydrochloride in 78 ml of DMF. The mixture was stirred overnight. LCMS control showed that the starting material had reacted completely, giving a 1:3.5 mixture of methyl 3-dibenzylaminocyclohexanoate and benzyl 3-dibenzylaminocyclohexanoate. About 150 ml each of water and MTBE were added to the reaction solution, the organic phase was separated off, the aqueous phase was extracted again with MTBE and the organic phases were combined. This organic phase was washed with about 100 ml of water and then with about 50 ml of saturated NaCl solution, dried over MgSO4 and concentrated. The residue was dried under reduced pressure, giving 23 g of the mixture as an oil. LCMS:

Workup

  1. customhad reacted completely
  2. customgiving
  3. customthe organic phase was separated off
  4. extractionthe aqueous phase was extracted again with MTBE
  5. washThis organic phase was washed with about 100 ml of water
  6. dry with materialwith about 50 ml of saturated NaCl solution, dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-558bf765115b4b728e84fe0bc9d6b870
Source dataset
uspto-grants-2009_10
Patent number
US07598281B2

Reaction notes

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