Hydroxyphenylacetic acid → HCID 69981182, compound

HRID 1369954Notes

Reaction equation

HRID 1369954 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:27]([NH:29][CH2:30][CH2:31][CH3:32])[CH3:28].Cl>O1CCCC1.C(OCC)(=O)C>[CH2:30]([N:29]([CH2:27][CH3:28])[C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH2:31][CH3:32]

Participants

8

Reactant 5

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 883981-Propanamine, N-ethyl-

Product 1

HCID 69981182HCID 69981182, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 4-hydroxyphenyl acetic acid (88.43 g, 653 mmol) in 700 mL tetrahydrofuran at −50° C. was added a solution of 4-methylmorpholine (66.1 g, 653 mmol) in 30 mL tetrahydrofuran. iso-Butylchloroformate (89.3 g, 653 mmol) was added to the mixture and the resulting solution was stirred at −50° C. for 2 hours. A solution of ethylpropylamine (57 g, 654 mmol) in 30 mL of tetrahydrofuran was added over 15 minutes. After 3 hours, the reaction mixture was poured into a 1:1 mixture of ethyl acetate and 1N hydrochloric acid. The ethyl acetate layer was washed with sodium bicarbonate and brine, then dried over sodium sulfate, filtered and concentrated to give a clear colorless oil (135 g). Purification of the technical grade material was accomplished by crystallization from ethyl acetate.

Workup

  1. waitAfter 3 hours
  2. washThe ethyl acetate layer was washed with sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d414950db8104a5696aa5046f98d6685
Source dataset
uspto-grants-2003_06
Patent number
US06579871B2

Reaction notes

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