Hydrochloric Acid → HCID 13957780, compound

HRID 847459Notes

Reaction equation

[H-].[Na+].CO.[Br:5][CH:6]([C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH:19]([F:21])[F:20])[N:12]=[C:11]([C:22]([F:25])([F:24])[F:23])[C:10]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:7]Br.Cl>C1COCC1>[Br:5][C:6]([C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH:19]([F:21])[F:20])[N:12]=[C:11]([C:22]([F:23])([F:24])[F:25])[C:10]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH2:7]

Participants

Conditions

Temperature: 5 °C

Procedure

To a stirred mixture of 0.49 g (0.012 mole) of 60% sodium hydride in oil dispersion and 4 ml of anhydrous THF is added 10 ml of methanol under nitrogen. The reaction mixture is cooled with an ice bath to 5° C. then treated slowly with a solution of 3.0 g (0.0058 mole) of product of Example 128 in 2 ml of anhydrous THF, while the reaction mixture is maintained below 15° C. The mixture is stirred at 0° C. for 2 hours and poured into 180 ml of 1% hydrochloric acid then extracted three times with 50 ml of methylene chloride. The combined methylene chloride extracts are dried over magnesium sulfate and concentrated. The residue is purified by a radially-accelerated preparatory TLC using 10% ethyl acetate/cyclohexane as eluent to give 0.85 g (33%) of the desired product as a light yellow oil, nD25 1.4734.

Workup

temperatureis maintained below 15° C
extractionthen extracted three times with 50 ml of methylene chloride
dry with materialThe combined methylene chloride extracts are dried over magnesium sulfate
concentrationconcentrated
customThe residue is purified by a radially-accelerated preparatory TLC

Sources & evidence

ORD record: ord-182fe479880d4bfa94a1e1fac0dd6fa5
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05142055

Reaction notes

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