Acetate-hydrochloric acid → HCID 51557049, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][C@@H:9]2[C:20]([O:22]C)=[O:21])=[CH:4][CH:3]=1.Cl.C(O)(=O)C>>[C:16]([O:15][C:13]([N:11]1[CH2:12][C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C@@H:9]([C:20]([OH:22])=[O:21])[CH2:10]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]Participants
3
Conditions
- Temperature
- 95 °C
Procedure
A mixture of the compound (2.7 g) obtained in step 3 and concentrated hydrochloric acid/acetic acid (4.2/4.2 mL) was stirred at 90 to 100° C. for 3 hr, and concentrated under reduced pressure. The residue was dissolved in DMAc (8.0 mL), Boc2O (2.8 g) and triethylamine (3.0 mL) were added at 0° C. and the mixture was stirred for 30 min. The mixture was poured into saturated aqueous ammonium chloride solution, and extracted twice with ethyl acetate. The extract was washed twice with water and with saturated brine, dried and concentrated under reduced pressure to give (3R*,4R*)-1-(tert-butoxycarbonyl)-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid (1.5 g, 56%) as a white powder.
Workup
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in DMAc (8.0 mL)
- additionBoc2O (2.8 g) and triethylamine (3.0 mL) were added at 0° C.
- stirringthe mixture was stirred for 30 min
- additionThe mixture was poured into saturated aqueous ammonium chloride solution
- extractionextracted twice with ethyl acetate
- washThe extract was washed twice with water and with saturated brine
- customdried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5d39d7797fe845659ee04ce843d203da
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592454B2
Reaction notes
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