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

HRID 51185

반응식

HRID 51185 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 22350042dichloromethane N,N-dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e79c5c77798049f2af95b4ccefdf6e6b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713602B1

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