Dichloromethane → N-(Carbamoylmethyl)-N-(thymin-1-ylacetyl)-beta-alanine ethyl ester

HRID 51185

Reaction equation

HRID 51185 reaction equation
[N:1]1([CH2:10][C:11]([OH:13])=O)[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].C(Cl)Cl.[CH2:17]([O:19][C:20](=[O:28])[CH2:21][CH2:22][NH:23][CH2:24][C:25](=[O:27])[NH2:26])[CH3:18].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CN(C=O)C.C(Cl)Cl>[CH2:17]([O:19][C:20](=[O:28])[CH2:21][CH2:22][N:23]([CH2:24][C:25](=[O:27])[NH2:26])[C:11](=[O:13])[CH2:10][N:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3])[CH3:18]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 22737577N-(Carbamoylmethyl)-beta-alanine ethylester

Product 1

HCID 22737569N-(Carbamoylmethyl)-N-(thymin-1-ylacetyl)-beta-alanine ethyl esterYield 61.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

DhbtOH (9.37 g, 57.4 mmol), N1-thyminyl acetic acid (10.57 g, 57.4 mmol) and CH2Cl2 (100 mL) were added to a solution of N-(carbamoylmethyl)-β-alanine ethylester (10.0 g, 57.4 mmol) in dry DMF (100 mL). The solution was cooled to 0° C. in an ice bath and a solution of DCC (1.90 g, 9.18 mmol) in DMF/CH2Cl2 (100 mL, 1:1 v/v) was added dropwise within 20 minutes. The ice bath was removed and after stirring for 1 hour at room temperature. The reaction mixture was filtered and the precipitate (DCU) was rinsed with CH2Cl2 (50 mL). The organic solution and the CH2Cl2 rinse were combined. A colorless precipitate formed overnight which was filtered and rinsed with CH2Cl2. The precipitate was dried in vacuo to give 12.0 g (61%) (mp 207-208° C.) of the title compound.

Workup

  1. customThe ice bath was removed
  2. filtrationThe reaction mixture was filtered
  3. washthe precipitate (DCU) was rinsed with CH2Cl2 (50 mL)
  4. washThe organic solution and the CH2Cl2 rinse
  5. customA colorless precipitate formed overnight which
  6. filtrationwas filtered
  7. washrinsed with CH2Cl2
  8. customThe precipitate was dried in vacuo

Sources & evidence

ORD record
ord-e79c5c77798049f2af95b4ccefdf6e6b
Source dataset
uspto-grants-2004_03
Patent number
US06713602B1

Linked notes

Loading…