HCID 178513479, compound → HCID 178454707, compound

HRID 2175725Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]([C@@H:8]2[C@@H:12]([OH:13])[C@H:11]([OH:14])[C@H:10]([CH2:15][OH:16])[O:9]2)[C:4]2=[N:17][C:18]([Br:23])=[C:19]([C:20]([NH2:22])=[O:21])[C:3]=12>N1C=CC=CC=1>[C:20]([O:16][CH2:15][C@H:10]1[C@H:11]([OH:14])[C@@H:12]([OH:13])[C@@H:8]([N:5]2[C:4]3=[N:17][C:18]([Br:23])=[C:19]([C:20](=[O:21])[NH2:22])[C:3]3=[C:2]([NH2:1])[N:7]=[CH:6]2)[O:9]1)(=[O:21])[CH:19]([CH3:3])[CH3:18]

Participants

Conditions

Temperature: -40 °C

Procedure

The compound of formula 1a (452 mg, 1.16 mmol) obtained in step 3 of Example 1 was dissolved in pyridine (5.8 mL) and then temperature was lowered to −40° C. Isobutyryl anhydride (193 μl, 1.16 mmol) was added to the above solution slowly by using a syringe pump for 1 hour. The reaction mixture was stirred at −40° C. for 6 hours and then the temperature was raised to room temperature, followed by extraction with water (20 mL) and ethyl acetate (20 mL) three times. The ethyl acetate extract was washed with saturated sodium_bicarbonate solution and brine and then dried over magnesium sulfate, followed by concentration. Flash chromatography was performed to give the target compound of formula 1b (215 mg, 0.47 mmol, 40%).

Workup

customwas lowered to −40° C
customfor 1 hour
temperaturethe temperature was raised to room temperature
extractionfollowed by extraction with water (20 mL) and ethyl acetate (20 mL) three times
extractionThe ethyl acetate extract
washwas washed with saturated sodium_bicarbonate solution and brine
dry with materialdried over magnesium sulfate
concentrationfollowed by concentration

Sources & evidence

ORD record: ord-008e41e797514613bb45118640dc5cc0
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062088B2

Reaction notes

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