Oxalyl chloride → HCID 63379722, compound

HRID 58621

Reaction equation

HRID 58621 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[NH2:18][C:19](=[N:25]O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(N(CC)C(C)C)(C)C>ClCCl.CN(C=O)C.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][C:9]1[O:11][N:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:18]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 676173-Fluorophenylacetic acidHCID 81531DiisopropylethylamineHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Product 1

HCID 63379722HCID 63379722, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

This compound was prepared according to general method 2 with (step I) 2-(3-fluorophenyl)acetic acid (1.03 g; 7.57 mmol) and oxalyl chloride (0.704 mL; 8.33 mmol) in dichloromethane (5 mL) and a few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino)acetate (1.0 g; 7.57 mmol) and N,N diisopropylethylamine (2.11 mL; 12.11 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 0.555 g (30%) of the title compound 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-48f48f8a6acc4a0991449a455fab8b72
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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