Carbon tetrabromide → HCID 18633461, 화합물

HRID 232373노트

반응식

HRID 232373 반응식
[F:1][C@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8]O)[O:4][C@H:3]1[N:10]1[CH:17]=[C:16]([CH2:18][CH3:19])[C:14](=[O:15])[NH:13][C:11]1=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:39]=[N+:40]=[N-:41].[Na+].C(Br)(Br)(Br)Br>CO.CN(C)C=O>[N:39]([CH2:8][C@H:5]1[O:4][C@@H:3]([N:10]2[CH:17]=[C:16]([CH2:18][CH3:19])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@@H:2]([F:1])[C@@H:6]1[OH:7])=[N+:40]=[N-:41]

참가 물질

7

반응물 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 1743161-(2-Deoxy-2-fluoroarabinofuranosyl)-5-ethyluracil

생성물 1

HCID 18633461HCID 18633461, 화합물수율 91.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 0.4 g of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyluracil, 0.44 g of triphenylphosphine, 0.48 g of sodium azide and 6 ml of dry dimethylformamide was stirred at room temperature under nitrogen while 0.48 g of carbon tetrabromide was added portionwise. The mixture was stirred at room temperature under nitrogen for 20 hours. 3 ml of methanol were added, the mixture was stirred for 0.5 hour and then evaporated. The residue was stirred for 0.5 hour with 8 ml of 0.5M sodium hydroxide solution. The resulting suspension was filtered and the insoluble triphenylphosphine oxide was washed with water. The filtrate was acidified to pH 5 by the addition of hydrochloric acid and then extracted three times with 20 ml of ethyl acetate. The extracts were dried over magnesium sulfate, filtered and evaporated. The residual solid was washed on to a filter with 10 ml of diethyl ether/petroleum ether (1:1) and then dried in vacuo to give 0.4 g of 1 -(5-azido-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyluracil as a white solid of melting point 185°-188° C.

후처리

  1. additionwas added portionwise
  2. stirringthe mixture was stirred for 0.5 hour
  3. customevaporated
  4. stirringThe residue was stirred for 0.5 hour with 8 ml of 0.5M sodium hydroxide solution
  5. filtrationThe resulting suspension was filtered
  6. washthe insoluble triphenylphosphine oxide was washed with water
  7. additionThe filtrate was acidified to pH 5 by the addition of hydrochloric acid
  8. extractionextracted three times with 20 ml of ethyl acetate
  9. dry with materialThe extracts were dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. washThe residual solid was washed on to
  13. filtrationa filter with 10 ml of diethyl ether/petroleum ether (1:1)
  14. customdried in vacuo

출처 및 근거

ORD 기록
ord-021dfd8af80a445883e362e69cf55ec4
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851519

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