Oxalyl chloride → HCID 66832125, compound

HRID 58645Notes

Reaction equation

HRID 58645 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]([OH:16])=O.C(Cl)(=O)C(Cl)=O.[NH2:23][C:24](=[N:30]O)[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(N(CC)C(C)C)(C)C>ClCCl.N1C=CC=CC=1.CN(C=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][C:14]1[O:16][N:30]=[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:23]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27751395-Methyl-2-phenyl-4-oxazoleacetic acidHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Product 1

HCID 66832125HCID 66832125, compoundYield 13%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

This compound was prepared according to general method 2 with (step I) 2-(5-methyl-2-phenyloxazol-4-yl)acetic acid (0.411 g; 1.89 mmol) and oxalyl chloride (0.176 mL; 2.08 mmol) in dichloromethane (12 mL) with few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino)acetate (0.250 g; 1.89 mmol) and N,N diisopropylethylamine (0.527 mL; 3.03 mmol) in dichloromethane (10 mL) and (step III) pyridine (18 mL). The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.076 g (13%) of ethyl 5-((5-methyl-2-phenyloxazol-4-yl)methyl)-1,2,4-oxadiazole-3-carboxylate as a white solid.

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-ddd5df7475a84ea9b9b07c977f57226a
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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