3-Amino-3-[4-benzyloxy-7-(4-chloro-phenylsulfanyl)-3-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-acrylic acid tert-butyl ester → HCID 10156578, compound

HRID 2213813Notes

Reaction equation

[C:1]([O:5][C:6](=[O:36])[CH:7]=[C:8]([NH2:35])[C:9]1(SC2C=CC(Cl)=CC=2)[CH2:16][C:15]2[C:10]1=[CH:11][C:12]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:13]([O:17][CH3:18])[CH:14]=2)([CH3:4])([CH3:3])[CH3:2]>ClC1C=CC=CC=1Cl>[C:1]([O:5][C:6]([C:7]1[C:8]([NH2:35])=[CH:9][C:10]2[C:15](=[CH:14][C:13]([O:17][CH3:18])=[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:11]=2)[CH:16]=1)=[O:36])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 179 °C

Procedure

Nitrogen gas is bubbled through a solution of 3-amino-3-[4-benzyloxy-7-(4-chloro-phenylsulfanyl)-3-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-acrylic acid tert-butyl ester (0.6 g, 1.1 mmol) in 1,2-dichlorobenzene (100 mL) for 1 hour and the reaction is heated to 179° C. After one hour the reaction is cooled and reduced in vacuo. The residue is washed with ether, dissolved in methylene chloride and purified through a plug of silica eluting with methylene chloride. The filtrate is reduced and dried to afford 0.321 g of 3-amino-6-benzyloxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester as a yellow solid, mp 179–180° C.

Workup

temperatureAfter one hour the reaction is cooled
washThe residue is washed with ether
dissolutiondissolved in methylene chloride
custompurified through a plug of silica eluting with methylene chloride
customdried

Sources & evidence

ORD record: ord-e36447f215fe40beb786d65ab0f86871
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105531B2

Reaction notes

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