Ethyl isocyanatoacetate → HCID 24830240, 화합물

HRID 2410045노트

반응식

HRID 2410045 반응식
[CH3:1][CH:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:10](=[O:11])[CH2:9][C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:6]1=[O:18].C(N(C(C)C)CC)(C)C.[N:29]([CH2:32][C:33]([O:35]CC)=[O:34])=[C:30]=[O:31]>ClCCl>[OH:11][C:10]1[N:5]([CH2:4][CH2:3][CH:2]([CH3:19])[CH3:1])[C:6](=[O:18])[N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:8](=[O:12])[C:9]=1[C:30]([NH:29][CH2:32][C:33]([OH:35])=[O:34])=[O:31]

참가 물질

5

반응물 3

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 18375361HCID 18375361, 화합물

생성물 1

HCID 24830240HCID 24830240, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

-{[6-Hydroxy-1,3-bis(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycine. A mixture of 1,3-bis(3-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione (1.2 g, 4.47 mmoles) and diisopropylethylamine (1.56 mL, 8.94 mmoles) was stirred in dichloromethane (30 mL) and treated with ethyl isocyanatoacetate (501 uL, 4.47 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 (430 mg, 26%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.09 (br. s, 1 H), 10.11 (s, 1 H), 4.09-4.16 (m, 2 H), 3.77-3.86 (m, 4 H), 1.51-1.62 (dt, J=13.29, 6.59, 6.59, 6.59, 6.59 Hz, 2 H), 1.42 (q, J=7.07 Hz, 4 H), 0.91 (d, J=6.57 Hz, 12 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 (430 mg, 26%)

출처 및 근거

ORD 기록
ord-6e7e951143ab4f6aae06267469ccbb34
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815884B2

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