Hydrochloric Acid → HCID 22329314, compound

HRID 587060Notes

Reaction equation

[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][C:26]#[C:27][CH3:28])[CH2:23][CH2:22][C:21]([C:29]([O:31]C)=[O:30])=[CH:20][C:19]=3[CH:33]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+].Cl>C1COCC1.CO>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][C:26]#[C:27][CH3:28])[CH2:23][CH2:22][C:21]([C:29]([OH:31])=[O:30])=[CH:20][C:19]=3[CH:33]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

In THF (5.0 ml)/methanol (5.0 ml) was dissolved methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(2-butynyl)-2,3-dihydro-1-benzazepine-4-carboxylate (0.50 g). To the solution was added 2N potassium hydroxide (5.0 ml), and the mixture was stirred at 50° C. for 3 hours. pH was adjusted to approximate 4 with 6N hydrochloric acid, and the solvent was concentrated to half under reduced pressure. The concentrated material was extracted with ethyl acetate, and the extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was washed with hexane/ethyl acetate (=8/1) to give 7-[4-(2-butoxyethoxy)phenyl]-1-(2-butynyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (0.40 g).

Workup

concentrationthe solvent was concentrated to half under reduced pressure
extractionThe concentrated material was extracted with ethyl acetate
washthe extract was washed with saturated brine
dry with materialdried with magnesium sulfate
customThe solvent was removed under reduced pressure
washthe resulting residue was washed with hexane/ethyl acetate (=8/1)

Sources & evidence

ORD record: ord-9809f2f518ca424c9051686931b90cab
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936602B1

Reaction notes

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