Trifluoroacetic acid → HCID 117843256, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][N:18]([C@@H](C3C=CC(O)=CC=3)C)[C:17](=[O:29])[CH2:16]2)[CH3:14])[C:5]2[S:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.C(O)(C(F)(F)F)=O>>[OH:1][C:2]1[CH:3]=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][NH:18][C:17](=[O:29])[CH2:16]2)[CH3:14])[C:5]2[S:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1Participants
3
Conditions
- Temperature
- 70 °C
Procedure
The crude product from Step 4 was dissolved in TFA (10 mL, 130 mmol). The resulting solution was heated to 70° C. After stifling 17 h, the reaction mixture was concentrated, and the resulting residue was dissolved in EtOAc (100 mL) and washed with a 1:1 mixture of brine and saturated NaHCO3 (100 mL). The phases were separated, and the aqueous phase was extracted with EtOAc (50 mL). The combined organic phase was dried over Na2SO4, filtered, and concentrated to afford (R)-4-((R)-1-(5-hydroxy-2-methylbenzo[d]thiazol-7-yloxy)ethyl)pyrrolidin-2-one that was used without further purification.
Workup
- concentrationthe reaction mixture was concentrated
- dissolutionthe resulting residue was dissolved in EtOAc (100 mL)
- washwashed with a 1:1 mixture of brine and saturated NaHCO3 (100 mL)
- customThe phases were separated
- extractionthe aqueous phase was extracted with EtOAc (50 mL)
- dry with materialThe combined organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b2fb4a66db52426fb64f81a9ffac6a4a
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376441B2
Reaction notes
Loading…