Ethanol → 5,11-Methenyltetrahydrohomofolate

HRID 2165715노트

반응식

HRID 2165715 반응식
C([NH:4][C:5]1[NH:6][C:7](=[O:39])[C:8]([CH2:15][CH2:16][CH2:17][NH:18][C:19]2[CH:38]=[CH:37][C:22]([C:23]([NH:25][C@H:26]([C:33]([O:35]C)=[O:34])[CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[O:24])=[CH:21][CH:20]=2)=[C:9]([NH:11]C(=O)C)[N:10]=1)(=O)C.C(O)C.[OH-].[Na+].N1C=CC=CC=1>O.C(O)CCC>[NH2:4][C:5]1[NH:6][C:7](=[O:39])[C:8]([CH2:15][CH2:16][CH2:17][NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([NH:25][C@H:26]([C:33]([OH:35])=[O:34])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:24])=[CH:37][CH:38]=2)=[C:9]([NH2:11])[N:10]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 1049PyridineHCID 14798Sodium HydroxideHCID 135990644HCID 135990644, 화합물

생성물 1

HCID 1354075895,11-Methenyltetrahydrohomofolate

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 962Water용매

실험 절차

A stirred solution of 1.60 g (2.89 mmol) of dimethyl N-[4-[3-(2,4-bis(acetamido)-1,6-dihydro-6-oxo-5-pyrimidinyl)propylamino]benzoyl]-L-glutamate, 50 ml of ethanol and 100 ml of 1N sodium hydroxide was heated at 50°-60° for 20 hours. The cooled reaction was spin evaporated in vacuo to 50 ml, cooled, and neutralized to pH 5-6 with concentrated hydrochloric acid. The resultant white precipitate was collected, washed with water, diethylether and dried; yield, 0.86 g (66%) mp (sinter 170°) 198°-202° (eff). Recrystallization from methanol gave the analytical sample; yield, 0.33 g (39%), mp (forms hard foam 180°) 200° (eff); TLC (pyridine:BuOH:H2O/1:1:1); NMR (DMSO-D6) δ8.07 (d, 1H, ArCONH), 7.65 (d, 2H, ArH), 6.54 (d, 2H, ArH), 6.22 (br s, 1H, CH2NH), 5.94 (s, 2H, NH2), 5.75 (s, 2H, NH2), 4.34 (m, 1H, CHCO2H), 3.03 (m, 2H, CH2NHAr), 2.30 (m, 4H, pyrimidine-CH2 and CH2CO2H), 2.03 (m, 2H, CHCH2), 1.58 (m, 2H, CH2CH2CH2).

후처리

  1. customThe cooled reaction
  2. customevaporated in vacuo to 50 ml
  3. temperaturecooled
  4. customThe resultant white precipitate was collected
  5. washwashed with water, diethylether
  6. customdried
  7. customyield
  8. custom0.86 g (66%) mp (sinter 170°) 198°-202° (eff)
  9. customRecrystallization from methanol
  10. customgave the analytical sample
  11. customyield
  12. custom0.33 g (39%), mp (forms hard foam 180°) 200° (eff)

출처 및 근거

ORD 기록
ord-3cc73388e96a4d04b11f90e321cada8d
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04940713

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