Carbon tetrabromide → HCID 18608979、化合物

HRID 1085530ノート

反応式

HRID 1085530 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 18608979HCID 18608979、化合物収率 51.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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-5ethyluridine in the form of a white solid which was processed directly without further purification.

後処理

  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

出典と根拠

ORDレコード
ord-9890c62c30ab4949aa5f7e5d6aef4a82
出典データセット
uspto-grants-1991_04
特許番号
US05010060

反応ノート

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