Triethylamine → HCID 178426653, compound

HRID 2037354Notes

Reaction equation

HRID 2037354 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]#[N:17])=[CH:11][C:10]=1[CH3:18])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:21][OH:22].C(N(CC)CC)C>CO>[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[C:10]([CH3:18])=[CH:11][C:12]([C:16](=[NH:17])[NH:21][OH:22])=[CH:13][C:14]=1[CH3:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 66935544Tert-butyl 3-(4-cyano-2,6-dimethylphenyl)propanoate

Product 1

HCID 178426653HCID 178426653, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-cyano-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (4.1 g, 15.8 mmol), hydroxylamine hydrochloride (1.65 g, 23.7 mmol) and triethylamine (3.20 g, 31.6 mmol) in methanol (40 mL) is refluxed for 2 h before the solvent is removed in vacuo. The residue is taken up in isopropyl acetate (50 mL) and washed twice with water (50 mL). The org. extract is dried over MgSO4, filtered, evaporated and dried to give 3-[4-(N-hydroxycarbamimidoyl)-2,6-dimethyl-phenyl]-propionic acid tert-butyl ester (4.4 g) as a white solid.

Workup

  1. customis removed in vacuo
  2. washwashed twice with water (50 mL)
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried

Sources & evidence

ORD record
ord-5e37f59b4e104f97a39e7f60befa420d
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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