Heptane → HCID 66739759, compound

HRID 1402745Notes

Reaction equation

HRID 1402745 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=O)=[CH:6][CH:5]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:26][C:27]([CH3:31])([CH3:30])[CH2:28][OH:29].CCCCCCC>ClCCl.CCOC(C)=O>[OH:29][CH2:28][C:27]([NH:26][C:8]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:13])=[CH:12][CH:11]=1)=[O:10])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 8900HeptaneHCID 118072-Amino-2-methyl-1-propanolHCID 682631,1'-CarbonyldiimidazoleHCID 36144541,4-Benzenedicarboxylic acid, methyl ester

Product 1

HCID 66739759HCID 66739759, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of mono-methylterephtalate (360 mg, 2.0 mmol) in dichloromethane (10 mL) under N2 was added 1,1′-carbonyldiimidazole (422 mg, 2.6 mmol) in one portion. The mixture was stirred at RT for 18 h. 2-Amino-2-methyl-1-propanol (232 mg, 2.6 mmol) was added as a solution in dichloromethane (1 mL) and stirring was continued for another 3 h. The reaction was quenched by pouring onto saturated aqueous NaHCO3 (50 mL). After extraction with dichloromethane (3×50 mL), the combined organic extracts were washed with brine (50 mL), dried (MgSO4), filtered and concentrated at reduced pressure. Purification by silica FCC (using a gradient of eluents; 7:3 to 1:1 heptane:EtOAc) gave the title compound (100 mg, 20% yield) as white solid.

Workup

  1. stirringstirring
  2. waitwas continued for another 3 h
  3. customThe reaction was quenched
  4. additionby pouring onto saturated aqueous NaHCO3 (50 mL)
  5. extractionAfter extraction with dichloromethane (3×50 mL)
  6. washthe combined organic extracts were washed with brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated at reduced pressure
  10. customPurification by silica FCC (

Sources & evidence

ORD record
ord-f520cf50f7844f7da3dc4bcc26e312df
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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