Hydrochloric Acid → 4-[(4E)-3-[2-(4-Carboxyphenyl)ethyl]-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]benzoic acid

HRID 1512222Notes

Reaction equation

HRID 1512222 reaction equation
[OH-].[Li+].C[O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH:15](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH2:37][CH2:38][CH2:39][N:40]2[CH2:44][CH2:43][CH2:42][C:41]2=[O:45])[CH2:16][CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)=[O:6].Cl>C1COCC1.O>[C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH:15](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH2:37][CH2:38][CH2:39][N:40]2[CH2:44][CH2:43][CH2:42][C:41]2=[O:45])[CH2:16][CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)([OH:6])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59437434HCID 59437434, compound

Product 1

HCID 250287024-[(4E)-3-[2-(4-Carboxyphenyl)ethyl]-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

18.5 mg (0.75 mmol) of lithium hydroxide are added to a solution of 150 mg (0.26 mmol) of methyl 4-[(4E)-3-{2-[4-(methoxycarbonyl)phenyl]ethyl}-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]-phenyl}pent-4-en-1-yl]benzoate in 10 ml of THF and 10 ml of water, and the mixture is stirred at 50° C. for 12 h. The mixture is then adjusted to pH 2 using 1 M hydrochloric acid and concentrated. The residue obtained is purified directly by preparative HPLC. This gives 104 mg (content 97%, 0.18 mmol, 71% of theory) of the title compound.

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. customis purified directly by preparative HPLC

Sources & evidence

ORD record
ord-91cecadcf8cf4ff8bd24970fca91bcfd
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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