Hydrochloric Acid → HCID 66942403, compound

HRID 536679Notes

Reaction equation

[Si]([C:5]([F:8])([F:7])[F:6])(C)(C)C.[C:9]([O:13][C:14]([N:16]1[CH2:23][CH2:22][C@:21]2([CH3:27])[C:24]([CH3:26])([CH3:25])[C@H:17]1[CH2:18][C:19]1[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][C:20]=12)=[O:15])([CH3:12])([CH3:11])[CH3:10].[F-].[Cs+].Cl.C([O-])([O-])=O.[K+].[K+]>O1CCCC1>[C:9]([O:13][C:14]([N:16]1[CH2:23][CH2:22][C@:21]2([CH3:27])[C:24]([CH3:25])([CH3:26])[C@H:17]1[CH2:18][C:19]1[CH:31]=[CH:30][C:29]([C:32]([OH:34])([CH3:33])[C:5]([F:8])([F:7])[F:6])=[CH:28][C:20]=12)=[O:15])([CH3:10])([CH3:11])[CH3:12]

Participants

Conditions

Temperature: -5 °C

Procedure

Me3SiCF3 (2 M in tetrahydrofuran, 0.42 mL) is added dropwise to a mixture of (2R,6S)-8-acetyl-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocine-3-carboxylic acid tert-butyl ester (0.30 g) and CsF (13 mg) in tetrahydrofuran (3 mL) cooled to ca. −5° C. The mixture is stirred at −5° C. for 1.5 h. Then, 1 M aqueous HCl solution (70 mL) is added and the mixture is stirred for 1 h. The mixture is basified using aqueous K2CO3 solution and then extracted with ethyl acetate. The combined organic extracts are washed with brine and dried (MgSO4). The solvent is evaporated to give the crude title compound that is submitted for cleaving the protective group without further purification.

Workup

stirringthe mixture is stirred for 1 h
extractionextracted with ethyl acetate
washThe combined organic extracts are washed with brine
dry with materialdried (MgSO4)
customThe solvent is evaporated

Sources & evidence

ORD record: ord-a7b19e9d7eb445dc8494dc7f92e33b8e
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859580B2

Reaction notes

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