Pyridine → HCID 20795491, compound

HRID 433674Notes

Reaction equation

HRID 433674 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:11]([O:13][C:14](=[O:34])[CH:15]([NH:27][C:28]([O:30][CH2:31][CH:32]=[CH2:33])=[O:29])[CH2:16][C:17]1[O:21][N:20]=[C:19]([CH:22]2[CH2:26][CH2:25][CH2:24][NH:23]2)[CH:18]=1)[CH3:12].N1C=CC=CC=1>ClCCl.C(OCC)(=O)C>[CH2:11]([O:13][C:14](=[O:34])[CH:15]([NH:27][C:28]([O:30][CH2:31][CH:32]=[CH2:33])=[O:29])[CH2:16][C:17]1[O:21][N:20]=[C:19]([CH:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:18]=1)[CH3:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 69735596HCID 69735596, compound

Product 1

HCID 20795491HCID 20795491, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzoyl chloride (21 μl, 0.18 mmol, 1.0 equivalents) was added in one portion to a solution of 2-allyloxycarbonylamino-3-(3-pyrrolidin-2-yl-isoxazol-5-yl)-propionic acid ethyl ester hydrochloride (1C) (74 mg, 0.20 mmol, 1.1 equivalents) in pyridine (29 μl, 0.36 mmol, 2.0 equivalents) and dichloromethane (2 mL) at 0° C. The reaction was stirred at room temperature for 4 hours then diluted with ethyl acetate (30 mL). The reaction was extracted with 1 N hydrochloric acid (30 mL) and brine (30 mL). The organic portion was dried over sodium sulfate and concentrated in vacuo to give the title compound (66 mg, 84%). MS (Cl) m/z 442.3 (M+1).

Workup

  1. extractionThe reaction was extracted with 1 N hydrochloric acid (30 mL) and brine (30 mL)
  2. dry with materialThe organic portion was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98b2b5d2293c48dcb7987b31097f4761
Source dataset
uspto-grants-2003_12
Patent number
US06667331B2

Reaction notes

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