N-(tert-butoxycarbonyl)glycine → Ethyl 3-(2-{(tert-butoxycarbonyl)amino}acetylamino)propionate

HRID 394005Notes

Reaction equation

HRID 394005 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:10]([O:14][C:15]([NH:17][CH2:18][C:19](O)=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 21893946Ethyl 3-(2-{(tert-butoxycarbonyl)amino}acetylamino)propionateYield 75.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 1.5 g of ethyl 3-aminopropionate monohydrochloride and 1.7 g of 2-{(tert-butoxycarbonyl)amino}acetic acid in 50 ml of chloroform, 1.6 g of 1-hydroxybenzotriazole monohydrate, 2.3 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride and 1.4 ml of triethylamine were added at room temperature by the order stated, and stirred for 2 hours at the same temperature. The reaction liquid was diluted with chloroform, and washed successively with saturated aqueous sodium bicarbonate solution, 10% aqueous citric acid solution and saturated saline solution, by the order stated, and dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/4) to provide 2.0 g of the title compound.

Workup

  1. customThe reaction liquid
  2. washwashed successively with saturated aqueous sodium bicarbonate solution, 10% aqueous citric acid solution and saturated saline solution, by the order
  3. dry with materialdried on anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resultant residue was purified by means of silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/4)

Sources & evidence

ORD record
ord-ccd09b6f84ba4a99937a316e7c400846
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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