Triethylamine → tert-butyl 3-[2-ethyl-4-[(Z)-N'-hydroxycarbamimidoyl]-6-methylphenyl]propanoate

HRID 2040806Notes

Reaction equation

HRID 2040806 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]#[N:17])=[CH:11][C:10]=1[CH2:18][CH3:19])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:22][OH:23].CCN(CC)CC>CO>[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16](=[NH:17])[NH:22][OH:23])=[CH:11][C:10]=1[CH2:18][CH3:19])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 685503513-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid tert-butyl ester

Product 1

HCID 178436624tert-butyl 3-[2-ethyl-4-[(Z)-N'-hydroxycarbamimidoyl]-6-methylphenyl]propanoateYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid tert-butyl ester (37.0 g, 135 mmol), hydroxylamine hydrochloride (14.1 g, 203 mmol) and NEt3 (27.4 g, 271 mmol) in MeOH (400 mL) is heated to reflux for 7 h before it is cooled to rt. The solvent is evaporated and the residue is taken up in isopropylacetate (500 mL) and washed twice with water (500 mL). The org. extract is dried over MgSO4, filtered, evaporated and dried to give 3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenyl]-propionic acid tert-butyl ester (40.8 g) as a pale yellow solid; 1H NMR δ 1.26 (t, J=7.5 Hz, 3 H), 1.49 (s, 9 H), 2.33-2.41 (m, 5 H), 2.66-2.74 (m, 2 H), 2.93-3.01 (m, 2 H), 4.85 (s, 1 H), 7.28 (s, 2 H).

Workup

  1. temperatureto reflux for 7 h before it
  2. customThe solvent is evaporated
  3. washwashed twice with water (500 mL)
  4. extractionextract
  5. dry with materialis dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried

Sources & evidence

ORD record
ord-02c73c91283a49d08cff96752d7d89f4
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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