Phosphorus oxychloride → HCID 58574145, compound
Reaction equation
[Cl:1][CH2:2][C:3]([NH:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1C(OC(C)(C)C)=O)=O.O=P(Cl)(Cl)Cl.[NH2:25][C:26]1[CH:34]=[C:33]([Br:35])[CH:32]=[CH:31][C:27]=1[C:28]([OH:30])=O>>[Br:35][C:33]1[CH:34]=[C:26]2[C:27]([C:28](=[O:30])[N:5]([CH2:6][CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][NH:8]3)[C:3]([CH2:2][Cl:1])=[N:25]2)=[CH:31][CH:32]=1Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A solution of tert-butyl 2-((2-chloroacetamido)methyl)piperidine-1-carboxylate (590 mg, 2.02 mmol) and POCl3 (5 mL) was stirred at room temperature for 30 min. Then 2-amino-4-bromobenzoic acid (442 mg, 1.94 mmol) was added to the mixture and stirred for another 20 min. After warming slowly to 100° C., the mixture was maintained at 100° C. for 1.5 h. Then the reaction mixture was poured into ice water, adjusted pH to 8 and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was directly used for the next reaction. MS (ESI): 370, 372 (MH+).
Workup
- temperaturethe mixture was maintained at 100° C. for 1.5 h
- extractionextracted with ethyl acetate (3×100 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationAfter filtration and concentration
- customthe crude product was directly used for the next reaction
Sources & evidence
- ORD record
- ord-b8261200d7ea482ab9a1a2296608fbb3
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772301B2
Reaction notes
Loading…