Diethyl Ether → 2,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-

HRID 2072852

반응식

HRID 2072852 반응식
[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=O)[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([OH:17])[C@H:11]2O)[CH:3]=1.C(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C(OCC)C>CN(C=O)C.CO.C(=O)(O)[O-].[Na+]>[CH3:1][C:2]1[C:8](=[O:9])[N:7]=[C:5]2[N:4]([C@@H:10]3[O:14][C@H:13]([CH2:15][OH:16])[C@H:12]([O:17]2)[CH2:11]3)[CH:3]=1

참가 물질

7

반응물 3

HCID 3283Diethyl EtherHCID 7597Diphenyl carbonateHCID 4454085-Methyluridine

생성물 1

HCID 4579822,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-수율 101.4%

시약·촉매·용매 3

HCID 516892Sodium Bicarbonate촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

A 100 mL round bottom flask equipped with magnetic stir bar, reflux condensor, and nitrogen inlet was charged with 5 g of ribothymidine, 4.7 g (1.2 eq) of diphenyl carbonate and 150 mg of sodium bicarbonate in 10 mL of DMF. The mixture was heated to 150° C. for 35 minutes. The black solution was diluted with 10 mL of MeOH and slowly added to 200 mL of diethyl ether. The tan product was filtered and dried to yield 4.4 g (96%) of anhydrothymidine.

후처리

  1. customA 100 mL round bottom flask equipped with magnetic stir bar
  2. temperaturereflux condensor, and nitrogen inlet
  3. filtrationThe tan product was filtered
  4. customdried

출처 및 근거

ORD 기록
ord-c0b3691bde8f4128a9160c5ebc5206ac
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04914233

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