1,2-Dichloroethane → HCID 22860739, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4](CC(O)=O)=[CH:3][CH:2]=1.CN1CC[O:15][CH2:14][CH2:13]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[F:32][C:33]([F:59])([F:58])[C:34]1[CH:35]=[C:36]([CH:51]=[C:52]([C:54]([F:57])([F:56])[F:55])[CH:53]=1)[CH2:37][O:38][C@H:39]1[O:44][CH2:43][CH2:42][NH:41][C@@H:40]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(Cl)Cl>[F:59][C:33]([F:32])([F:58])[C:34]1[CH:35]=[C:36]([CH:51]=[C:52]([C:54]([F:55])([F:56])[F:57])[CH:53]=1)[CH2:37][O:38][C@H:39]1[O:44][CH2:43][CH2:42][N:41]([C:14]([CH2:13][C:5]2[CH:6]=[N:1][CH:2]=[CH:3][CH:4]=2)=[O:15])[C@@H:40]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1Participants
7
Procedure
A solution of 55 mg (0.315 mmol) of 4-pyridylacetic acid in 1 mL of CH2Cl2, containing 0.079 mL (0.715 mmol) of N-methylmorpholine, 53 mg (0.37 mmol) of HOBt and 73 mg (0.37 mmol) of EDC was stirred for 10 min. A solution of 2-(S)-(3,5-bis(tri-fluoromethyl)benzyloxy)-3-(R)-phenylmorpholine (from Example 33) in 1 mL of CH2Cl2 was added. After stirring the mixture for 2 h, it was partitioned between water and CH2C12. The organic layer was washed with water, brine and dried by filtering through Na2SO4. The filtrate was concentrated and the residue was purified by flash chromatography using 70% EtOAc/hexane to furnish 152 mg (100% yield) of the product.
Workup
- stirringAfter stirring the mixture for 2 h
- customit was partitioned between water and CH2C12
- washThe organic layer was washed with water, brine
- customdried
- filtrationby filtering through Na2SO4
- concentrationThe filtrate was concentrated
- customthe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-a03fe6e671c94b4eba3197d7b32f22de
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05872116
Reaction notes
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