Hydrochloric Acid → HCID 19598008, compound

HRID 611692Notes

Reaction equation

HRID 611692 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[F:18][C:19]([F:24])([F:23])[C:20](O)=[O:21].Cl>O1CCCC1.C(N(CC)CC)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:20](=[O:21])[C:19]([F:24])([F:23])[F:18])=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 15029691HCID 15029691, compound

Product 1

HCID 19598008HCID 19598008, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

t-Butyl 3-(1-hydroxy-4-aminobenzen-2-yl)propionate was dissolved in a mixture of tetrahydrofuran (100 ml) and triethylamine (7.1 ml). Anhydrous trifluoroacetic acid (6.0 ml) was added to the solution at 0° C. in an atmosphere of argon gas. The solution was stirred for 2 hr. at 0°0 C. The reaction solution was poured into a mixture of ice and 1N hydrochloric acid (100 ml). The reaction mixture was extracted with ethyl acetate (300 ml). The extract was washed with water, saturated aqueous solution of sodium bicarbonate, followed by brine, dried over anhydrous magnesium sulfate and evaporated. The residue was recrystallized from a mixture of ethyl acetate-n-hexane (1:5) to give the title compound having the following physical data.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (300 ml)
  2. washThe extract was washed with water, saturated aqueous solution of sodium bicarbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from a mixture of ethyl acetate-n-hexane (1:5)

Sources & evidence

ORD record
ord-e1884be272de4071951be4f11eb1470c
Source dataset
uspto-grants-1999_12
Patent number
US06001877

Reaction notes

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