Lithium Hydroxide → HCID 9867259, compound

HRID 2299199Notes

Reaction equation

[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[CH2:23][C@@H:22]([CH2:24][C:25]([O:27]CC)=[O:26])[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[CH2:19][C:18]=2[CH:34]=1.[Li+].[OH-]>C1COCC1.O>[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[CH2:23][C@@H:22]([CH2:24][C:25]([OH:27])=[O:26])[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[CH2:19][C:18]=2[CH:34]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl (S)-10,11-dihydro-3-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-1-ethoxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (131 mg, 0.29 mmole) in THF/H2O (2 mL) was added 1.0 N LiOH (0.43 mL, 0.43 mmole), and the mixture was heated to 50° C. After 18 hr, the mixture was cooled to RT and washed with Et2O (2×2 mL). The aqueous layer was acidified to pH 6 using 10% HCl. The resulting milky solution was passed through a C-18 bond-elute column (gradient elution: H2O, then 20% CH3CN/H2O, then CHCl3 as eluent). Fractions containing the product were concentrated under reduced pressure to give the title compound (30 mg, 24%) as a white powder: MS (ES) m/e 429 (M+H)+. Anal. Calcd for C27H28N2O3.0.95 HCl: C, 70.02; H, 6.30; N, 6.05. Found: C, 70.01; H, 6.33; N, 5.71.

Workup

temperaturethe mixture was cooled to RT
washwashed with Et2O (2×2 mL)
washbond-elute column (
washgradient elution
additionFractions containing the product
concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record: ord-bfbe41f95e0e4e46aa3721e7743a82df
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495560B1

Reaction notes

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