Thymine → (2R,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-(thymin-1-yl)-2,5-dihydrofuran

HRID 1503307노트

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HRID 1503307 반응식
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[C:10]([O:14][C:15]([O:17][CH2:18][C@@:19]1([C:32]#[CH:33])[O:23][C@@H:22](OC(OC(C)(C)C)=O)[CH:21]=[CH:20]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]([O:14][C:15]([O:17][CH2:18][C@@:19]1([C:32]#[CH:33])[O:23][C@@H:22]([N:1]2[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]2=[O:3])[CH:21]=[CH:20]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

참가 물질

5

반응물 2

HCID 1135ThymineHCID 53372554(2S,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-t-butoxycarbonyloxy-2,5-dihydrofuran

생성물 1

HCID 53372555(2R,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-(thymin-1-yl)-2,5-dihydrofuran수율 72%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매2회

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온도
55 °C

실험 절차

Thymine (16.7 g), N,N′-dimethylformamide (162 g), and tetrakis(triphenylphosphine)palladium(0) (917 mg) were added to a glass reactor under nitrogen, and the mixture was heated to 55° C. Then, a solution of (2S,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-t-butoxycarbonyloxy-2,5-dihydrofuran (β/α=>99/1) (9.0 g) in N,N′-dimethylformamide was added dropwise thereto, and the mixture was stirred for 30 minutes. The reaction mixture was filtered, and water was added to the filtrate, followed by stirring for phase separation. The thus-separated organic layer was concentrated. The residue was purified through recrystallization from acetonitrile and toluene, to thereby yield 6.5 g of (2R,5R)-5-t-butoxycarbonyloxymethyl-5-ethynyl-2-(thymin-1-yl)-2,5-dihydrofuran (yield: 72%, β/α=>99/1). The 1H-NMR data of the compound are as follows.

후처리

  1. filtrationThe reaction mixture was filtered
  2. additionwater was added to the filtrate
  3. stirringby stirring for phase separation
  4. concentrationThe thus-separated organic layer was concentrated
  5. customThe residue was purified through recrystallization from acetonitrile and toluene

출처 및 근거

ORD 기록
ord-df253cb17a4d492dbb6df74ec33400d0
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212174B2

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