Carbon tetrabromide → HCID 18608979, 화합물

HRID 232361노트

반응식

HRID 232361 반응식
[CH2:1]([C:3]1[C:4](=[O:17])[NH:5][C:6](=[O:16])[N:7]([CH:15]=1)[C@@H:8]1[O:14][C@H:11]([CH2:12]O)[CH2:10][CH2:9]1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:37]=[N+:38]=[N-:39].[Na+].C(Br)(Br)(Br)Br>CO>[N:37]([CH2:12][C@H:11]1[O:14][C@@H:8]([N:7]2[CH:15]=[C:3]([CH2:1][CH3:2])[C:4](=[O:17])[NH:5][C:6]2=[O:16])[CH2:9][CH2:10]1)=[N+:38]=[N-:39]

참가 물질

6

반응물 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 4514525-Et-ddU

생성물 1

HCID 18608979HCID 18608979, 화합물수율 51.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 350 mg of 2',3'-dideoxy-5-ethyluridine, 391 mg of triphenylphosphine, 475 mg of sodium azide and 496 mg of carbon tetrabromide was stirred at room temperature for 20 hours. 3 ml of methanol were added, the mixture was stirred for 1 hour and then evaporated. The residue was suspended in 30 ml of water and extracted twice with 50 ml of ethyl acetate each time. The combined ethyl acetate extracts were washed with 20 ml of water and then evaporated. The residue was subjected to flash chromatography on a column of silica gel using ethyl acetate for the elution. The product was crystallized from a mixture of ethyl acetate and hexane to give 200 mg of 5'-azido-2',3',5'-trideoxy-5-ethyluridine in the form of a white solid which was processed directly without further purification.

후처리

  1. stirringthe mixture was stirred for 1 hour
  2. customevaporated
  3. extractionextracted twice with 50 ml of ethyl acetate each time
  4. washThe combined ethyl acetate extracts were washed with 20 ml of water
  5. customevaporated
  6. washfor the elution
  7. customThe product was crystallized from a mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-453613ff9a6341bbaea442a6dd1c8d27
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851519

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