Hydrochloric Acid → (3-Cyclohexylcarbamoylmethyl-phenyl)-acetic acid

HRID 553301Notes

Reaction equation

HRID 553301 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([CH2:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19](O)=[O:20])[CH:15]=[CH:16][CH:17]=1)([OH:10])=[O:9].ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.Cl.CN(C)CCCN=C=NCC.Cl>ClCCl>[CH:1]1([NH:7][C:19]([CH2:18][C:14]2[CH:13]=[C:12]([CH2:11][C:8]([OH:10])=[O:9])[CH:17]=[CH:16][CH:15]=2)=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 29788m-Phenylenediacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67165667(3-Cyclohexylcarbamoylmethyl-phenyl)-acetic acidYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclohexylamine (510 mg), (3-carboxymethyl-phenyl)-acetic acid (1.0 g), 1-hydroxybenzotriazole (700 mg) and Hunigs base (0.9 mL) were added to a round bottomed flask and dissolved in dichloromethane (40 mL) at room temperature. The mixture was stirred at room temperature for 5 minutes then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (990 mg) was added. The reaction was stirred at room temperature for 3 hours. The mixture was diluted with dichloromethane (40 mL) and washed with 2M hydrochloric acid (2×40 mL). The organic layer was isolated and extracted with 2M sodium hydroxide (2×40 mL). The basic extract was isolated, acidified with 2M hydrochloric acid and extracted with dichloromethane (2×40 mL). The dichloromethane extracts were combined, dried over anhydrous sodium sulphate, filtered and concentrated to give 626 mg of the sub-titled product as a white solid.

Workup

  1. stirringThe reaction was stirred at room temperature for 3 hours
  2. washwashed with 2M hydrochloric acid (2×40 mL)
  3. customThe organic layer was isolated
  4. extractionextracted with 2M sodium hydroxide (2×40 mL)
  5. extractionThe basic extract
  6. customwas isolated
  7. extractionextracted with dichloromethane (2×40 mL)
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f76f0c5537fa4b4fbdd94127f66877bb
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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