Dichloromethane → HCID 131725969, compound

HRID 1242555Notes

Reaction equation

HRID 1242555 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[CH2:8][N:7](C(OC(C)(C)C)=O)[C@H:6]([C:16]2[O:20][N:19]=[C:18]([CH3:21])[N:17]=2)[CH2:5]1.C(Cl)[Cl:23]>>[ClH:23].[CH3:1][O:2][N:3]=[C:4]1[CH2:5][C@@H:6]([C:16]2[O:20][N:19]=[C:18]([CH3:21])[N:17]=2)[NH:7][CH2:8]1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 131725968HCID 131725968, compound

Product 1

HCID 131725969HCID 131725969, compound

Procedure

A solution was made containing tert-butyl (2S,4EZ)-4-(methoxyimino)-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1-pyrrolidinecarboxylate (1.26 g, 4.25 mmol) in anhydrous DCM (120 ml). At 0° C., HCl gas, previously dried with a H2SO4 cc trap, was bubbled slowly through the reaction and deprotection was monitored by TLC using cyclohexane/ethyl acetate (1/1) and stained with a pancaldi solution. After approximately 45 minutes, TLC showed no remaining starting materiel and DCM was then evaporated under vacuo without heating to avoid pyrolidine salt decomposition. More DCM (20 ml) was then added and evaporated again under vacuo to remove remaining potential HCl (2–3 times). The desired product, (3EZ,5S)-5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyrrolidinone O-methyloxime, hydrochloride salt, was isolated as a white solid and used without further purification and characterization

Workup

  1. dry with materialAt 0° C., HCl gas, previously dried with a H2SO4 cc trap
  2. customwas bubbled slowly through the reaction and deprotection
  3. customwas then evaporated under vacuo
  4. temperaturewithout heating
  5. additionMore DCM (20 ml) was then added
  6. customevaporated again under vacuo
  7. customto remove

Sources & evidence

ORD record
ord-ec134f7cdb1b4cc287b5919fcb159610
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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