Hydrochloric Acid → HCID 57864382, compound

HRID 1672650Notes

Reaction equation

[C:1]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:12]=2[C:13](O)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+].Cl>C1COCC1.CO>[C:1]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:12]=2[CH2:13][OH:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

6.65 g (22 mmol) of 2-(4-tert-butylbenzyloxy)-5-fluorobenzoic acid are suspended in 25 ml of THF and cooled to 0° C. 2.4 ml (22 mmol) of N-methylmorpholine and 2.1 ml (22 mmol) of ethyl chloroformate are added, and the solution is stirred at room temperature for 15 min. 2.50 g (66 mmol) of sodium borohydride are added and, after 3 h, methanol is added until gas evolution has subsided. The mixture is acidified with 1 N hydrochloric acid and concentrated in vacuo, and the residue is taken up in ethyl acetate. The organic phase is washed with saturated sodium chloride solution and then dried over sodium sulfate. The solvent is distilled out in vacuo, and the residue is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 3.52 g (12.2 mmol, 55% of theory) of the title compound are isolated.

Workup

concentrationconcentrated in vacuo
washThe organic phase is washed with saturated sodium chloride solution
dry with materialdried over sodium sulfate
distillationThe solvent is distilled out in vacuo
customthe residue is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record: ord-b61cbaeb0653456f97293fc258ff9760
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998988B2

Reaction notes

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