Dichloromethane → HCID 57617721, compound

HRID 1670420Notes

Reaction equation

[OH:1][C@@H:2]1[C@H:6]([C@H:7]([OH:14])/[CH:8]=[CH:9]/[C:10]([CH3:13])([CH3:12])[CH3:11])[O:5][C:4](=[O:15])[C@@H:3]1[O:16][CH3:17].[NH2:18][CH:19]1[N:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]2[CH:32]=[CH:33][CH:34]=[CH:35][C:22]=2[NH:21][C:20]1=[O:36].C(C(CCCC)C([O-])=O)C.[Na+].C(Cl)Cl>C1COCC1>[O:36]=[C:20]1[CH:19]([NH:18][C:4](=[O:15])[C@H:3]([O:16][CH3:17])[C@H:2]([OH:1])[C@@H:6]([OH:5])[C@H:7]([OH:14])/[CH:8]=[CH:9]/[C:10]([CH3:13])([CH3:12])[CH3:11])[N:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]2[CH:32]=[CH:33][CH:34]=[CH:35][C:22]=2[NH:21]1

Participants

Conditions

Temperature: 60 °C

Procedure

235 mg of 2 (818 μmol), 400 mg of 14 (1.59 mmol), 340 mg of sodium 2-ethylhexanoate (2.04 mmol) in 3.5 mL of THF are successively introduced into a 30 mL round-bottomed flask, with stirring and under an argon atmosphere. The mixture is heated at 60° C. for 5 h and the stirring is maintained at RT for 24 h. 15 mL of CH2Cl2 are added to the reaction medium. The mixture is washed with twice 10 mL of HCl (1N) and then 10 mL of a saturated aqueous NaCl solution. The organic phase is dried over anhydrous magnesium sulphate, filtered and then evaporated to dryness. 510 mg of crude product are obtained, which product is chromatographed on a silica cartridge (30 g, eluent CH2Cl2/MeOH 97/3). 73 mg of expected product Ex6 are recovered.

Workup

temperaturethe stirring is maintained at RT for 24 h
washThe mixture is washed with twice 10 mL of HCl (1N)
dry with materialThe organic phase is dried over anhydrous magnesium sulphate
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-13062ea9d50742ccac4efa8fc18274e2
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994161B2

Reaction notes

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