Pyridine → HCID 22398118, compound

HRID 1071283Notes

Reaction equation

HRID 1071283 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([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)C.N1C=CC=CC=1>ClCCl.C(OCC)(=O)C>[CH2:31]([O:30][C:28]([NH:27][CH:15]([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)[C:14]([OH:34])=[O:13])=[O:29])[CH:32]=[CH2:33]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 69735596HCID 69735596, compound

Product 1

HCID 22398118HCID 22398118, compoundYield 88.7%

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 1N 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 1N 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-a7d9627777054ffe89aad29a5b72c672
Source dataset
uspto-grants-2005_06
Patent number
US06903128B2

Reaction notes

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