Triethylamine → Ethyl 3-(3-ethoxy-3-oxopropanamido)-3-methylbutanoate

HRID 1180085Notes

Reaction equation

HRID 1180085 reaction equation
Cl.[NH2:2][C:3]([CH3:11])([CH3:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.Cl[C:20](=[O:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(Cl)Cl>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:20]([NH:2][C:3]([CH3:11])([CH3:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 15578558Ethyl 3-amino-3-methylbutanoate hydrochloride

Product 1

HCID 25193721Ethyl 3-(3-ethoxy-3-oxopropanamido)-3-methylbutanoateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-amino-3-methylbutanoate hydrochloride (0.87 g, 4.79 mmol) was suspended on methylene chloride (12 mL) and triethylamine (1.4 mL, 2.1 eq.). The mixture was cooled to 0° C. and treated dropwise with ethyl 3-chloro-3-oxopropanoate (0.64 mL, 1.05 eq.). The reaction was kept at room temperature for 2 hours, diluted with methylene chloride, washed with 1 N HCl and then with 5% NaHCO3, dried over Na2SO4 and evaporated to dryness to obtain ethyl 3-[(3-ethoxy-3-oxopropanoyl)amino]-3-methylbutanoate (1.2 g, Y=97%) as a red oil.

Workup

  1. washwashed with 1 N HCl
  2. dry with materialwith 5% NaHCO3, dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-abf86e69b8eb4286999f3d6bf40a9578
Source dataset
uspto-grants-2007_10
Patent number
US07279575B2

Reaction notes

Loading…