Triethylamine → HCID 178426653, compound

HRID 2047298Notes

Reaction equation

HRID 2047298 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-d2252643a3474769b61adfa8aabcbd25
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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