Water → HCID 86753834, compound

HRID 1417626Notes

Reaction equation

C(O[C@@H:5]1[C@H:27](O)[C:26]([CH3:30])([CH3:29])[C@H:25]2[C@@:7]3([O:21][C:11]4[C:12]5[CH2:13][NH:14][C:15](=[O:20])[C:16]=5[CH:17]=[C:18]([OH:19])[C:10]=4[CH2:9][C@:8]3([CH3:32])[C@@H:22]([CH3:31])[CH2:23][CH2:24]2)[CH2:6]1)(=O)C.N1C=CC=CC=1.Cl.[NH2:40][OH:41].O>C(O)C>[OH:19][C:18]1[C:10]2[CH2:9][C@:8]3([CH3:32])[C@@H:22]([CH3:31])[CH2:23][CH2:24][C@H:25]4[C:26]([CH3:29])([CH3:30])[C:27](=[N:40][OH:41])[CH2:5][CH2:6][C@@:7]34[O:21][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:20])[C:16]=2[CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of Compound (12) (Step-2 of Example 55) (30 mg, 0.078 mmol) in 3.0 ml of ethanol were added 0.3 ml (3.70 mmol) of pyridine and 9 mg (0.13 mmol) of hydroxylamine hydrochloride, and the mixture stirred for 3 hours at 80° C. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed sequentially with 1N HCl, water, an aqueous saturated sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The crystalline residue was recrystallized from diethyl ether-pentane to give 26 mg (83%) of Compound (51a).

Workup

extractionthe reaction mixture was extracted with ethyl acetate
washThe extract was washed sequentially with 1N HCl, water
dry with materialan aqueous saturated sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe crystalline residue was recrystallized from diethyl ether-pentane

Sources & evidence

ORD record: ord-58f2876fbd7849f9a5c7f3b07220d0a9
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05876984

Reaction notes

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