Ethyl isocyanatoacetate → N-[(6-Hydroxy-1,3-bis{[2-(methyloxy)phenyl]methyl}-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)carbonyl]glycine

HRID 2410047노트

반응식

HRID 2410047 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[C:15](=[O:16])[CH2:14][C:13](=[O:17])[N:12]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[C:11]1=[O:27].C(N(C(C)C)CC)(C)C.[N:37]([CH2:40][C:41]([O:43]CC)=[O:42])=[C:38]=[O:39]>ClCCl>[OH:17][C:13]1[N:12]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[C:11](=[O:27])[N:10]([CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:15](=[O:16])[C:14]=1[C:38]([NH:37][CH2:40][C:41]([OH:43])=[O:42])=[O:39]

참가 물질

5

반응물 3

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 233034641,3-bis(2-methoxybenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione

생성물 1

HCID 24830241N-[(6-Hydroxy-1,3-bis{[2-(methyloxy)phenyl]methyl}-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)carbonyl]glycine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-[(6-hydroxy-1,3-bis{[2-(methyloxy)phenyl]methyl}-2,4-dioxo-1,2,34-tetrahydro-5-pyrimidinyl)carbonyl]glycine. A mixture of 1,3-bis{[2-(methyloxy)phenyl]methyl}-2,4,6(1H,3H,5H)-pyrimidinetrione (1.64 g, 4.45 mmoles) and diisopropylethylamine (1.56 mL, 8.94 mmoles) was stirred in dichloromethane (30 mL) and treated with ethyl isocyanatoacetate (500 uL, 4.45 mmoles). The mixture was stirred for 5 hours, washed with 1 molar hydrochloric acid (×2), evaporated, taken up in ethanol-6 molar sodium hydroxide and stirred overnight. The mixture was acidified and extracted into ethyl acetate (×2). The extracts were washed with 1 molar hydrochloric acid evaporated, dried and evaporated. The title compound was recrystallized from acetic acid (1.0 g, 48%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.51 (br. s., 1 H), 10.11 (t, J=4.93 Hz, 1 H), 7.20-7.28 (m, 2 H), 7.00 (d, J=7.83 Hz, 2 H), 6.86-6.96 (m, 4 H), 5.00 (s, 4 H), 4.10-4.18 (m, 2 H), 3.82 (s, 6 H).

후처리

  1. washwashed with 1 molar hydrochloric acid (×2)
  2. customevaporated
  3. stirringstirred overnight
  4. extractionextracted into ethyl acetate (×2)
  5. washThe extracts were washed with 1 molar hydrochloric acid
  6. customevaporated
  7. customdried
  8. customevaporated
  9. customThe title compound was recrystallized from acetic acid (1.0 g, 48%)

출처 및 근거

ORD 기록
ord-ea015ea81a674318999d863477e631c1
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815884B2

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