Acetic Acid → HCID 86714685, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][C@@H:13]2[CH2:17][C@H:16]([O:18][CH2:19][C:20]([O-:22])=[O:21])[C@@H:15]([OH:23])[C@H:14]2[OH:24])[C:3]=1[N+:25]([O-])=O.CO.[C:30](O)(=O)[CH3:31]>>[NH2:25][C:3]1[C:4]([NH:12][C@@H:13]2[CH2:17][C@H:16]([O:18][CH2:19][C:20]([O:22][CH2:30][CH3:31])=[O:21])[C@@H:15]([OH:23])[C@H:14]2[OH:24])=[N:5][C:6]([S:8][CH2:9][CH2:10][CH3:11])=[N:7][C:2]=1[Cl:1]Participants
Conditions
- Temperature
- 27.5 °C
Procedure
Compound 7a (5 g, 0.011 mol) was added to methanol (25 mL) at 25-30° C. Acetic acid (15 mL) was added slowly to the reaction mixture over 30 min. The reaction mixture was stirred at 25-30° C. for 2 h. After 2 hrs, the reaction was monitored by TLC and showed completion. The reaction mixture was passed through a diatomaceous earth (Celite) pad and the pad was washed with methanol (25 mL). The filtrate was concentrated under reduced pressure at 50° C. The thus obtained residue was mixed with water (50 mL) and basified with aqueous NaHCO3 to pH 9.0. The aqueous layer was extracted with ethyl acetate (3×25 mL). The combined extract was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to provide the crude product (89%), which was used for next step without further purification.
Workup
- waitAfter 2 hrs
- washthe pad was washed with methanol (25 mL)
- concentrationThe filtrate was concentrated under reduced pressure at 50° C
- additionThe thus obtained residue was mixed with water (50 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (3×25 mL)
- extractionThe combined extract
- washwas washed with brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6c8a6f7a162f420b9dba64fcd90f08e5
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056838B2
Reaction notes
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