Hydrochloric Acid → HCID 56592202, compound

HRID 535264Notes

Reaction equation

HRID 535264 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:30]=[CH:31][CH:32]=1)[O:8][CH2:9][C:10]1([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([C:27]#[C:28][CH3:29])[CH2:22][C:23]([O:25]C)=[O:24])=[CH:17][CH:16]=2)[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].Cl.O>C1COCC1.CO>[C:1]([C:5]1[CH:6]=[C:7]([CH:30]=[CH:31][CH:32]=1)[O:8][CH2:9][C:10]1([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]([C:27]#[C:28][CH3:29])[CH2:22][C:23]([OH:25])=[O:24])=[CH:19][CH:20]=2)[CH2:12][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 58031830HCID 58031830, compound

Product 1

HCID 56592202HCID 56592202, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

410 mg of methyl 3-{4-[1-(3-tert-butylphenoxymethyl)cyclopropylmethoxy]phenyl}hex-4-ynoate were dissolved in a mixture of THF/MeOH/2N NaOH=1:1:1 (5 ml of each) and stirred at room temperature. After 45 min, the mixture was acidified to pH 1 by adding 4N HCl. 50 ml of water were added, the mixture was extracted three times with 50 ml each time of ethyl acetate. The combined organic phases were dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by means of RP-HPLC. This gave 148 mg of 3-{4-[1-(3-tert-butylphenoxymethyl)cyclopropylmethoxy]phenyl}hex-4-ynoic acid.

Workup

  1. extractionthe mixture was extracted three times with 50 ml each time of ethyl acetate
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by means of RP-HPLC

Sources & evidence

ORD record
ord-8e01e5112c7a491ea78f4a6f115b8bb0
Source dataset
uspto-grants-2014_10
Patent number
US08859494B2

Reaction notes

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