Hydrochloric Acid → HCID 86757493, compound

HRID 380646Notes

Reaction equation

[OH:1][C@:2]1(CO)[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3]1.ClC1C=C(N(C2C=CC=CC=2)C(Cl)=O)C=CC=1.Cl>N1C=CC=CC=1>[CH2:17]([O:16][C:14]([CH2:13][O:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH2:10][CH2:11][CH:2]([OH:1])[CH2:3]2)=[O:15])[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (2R)-2-hydroxy-2-(hydroxymethyl)-5-[(ethoxy carbonyl)methoxy]-1,2,3,4-tetrahydronaphthalene (465 mg) and N-(3-chlorophenyl)-N-phenylcarbamoyl chloride (2.21 g) in pyridine (10 mL) was stirred at 100° C. for 24 hours. After cooling, the reaction mixture was poured into 3N hydrochloric acid (50 mL) under ice-cooling and extracted with EtOAc The organic layer was washed with water, saturated sodium hydrogen carbonate, water, and brine, dried over magnesium sulfate, evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 3:2) to give (2R)-2-{N-(3-chlorophenyl)-N-phenylcarbamoyloxy]methyl}-5-[(ethoxycarbonyl)methoxy]-2-hydroxy-1,2,3,4-tetrahydronaphthalene (800.6 mg) as a solid.

Workup

temperatureAfter cooling
temperaturecooling
extractionextracted with EtOAc The organic layer
washwas washed with water, saturated sodium hydrogen carbonate, water, and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (hexane-EtOAc 3:2)

Sources & evidence

ORD record: ord-d8c7ba40b84442cf838b8edde104b24f
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303649B1

Reaction notes

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