Carbon tetrabromide → 5'-Azido-2',5'-dideoxy-5-(2-chloroethyl)uridine

HRID 1085534

反応式

HRID 1085534 の反応式
[Cl:1][CH2:2][CH2:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14]O)[C@@H:11]([OH:12])[CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:39]=[N+:40]=[N-:41].[Li+].C(Br)(Br)(Br)Br>CN(C)C=O.CO>[N:39]([CH2:14][C@H:13]1[O:16][C@@H:9]([N:8]2[CH:17]=[C:4]([CH2:3][CH2:2][Cl:1])[C:5](=[O:19])[NH:6][C:7]2=[O:18])[CH2:10][C@@H:11]1[OH:12])=[N+:40]=[N-:41]

参加物

7

反応物 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 88163Lithium azideHCID 5148145-(2-Chloroethyl)-2'-deoxyuridine

生成物 1

HCID 540023075'-Azido-2',5'-dideoxy-5-(2-chloroethyl)uridine収率 31.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

1.4 g of 5-(2-chloroethyl)-2'-deoxyuridine and 1.3 g of triphenylphosphine were dissolved in 20 ml of dimethylformamide and stirred while 1.2 g of lithium azide were added to give a solution within 5 minutes at room temperature. 1.7 g of carbon tetrabromide were added portionwise during 5 minutes to give a hazy orange colored solution which was stirred at room temperature for 17 hours. 5 ml of methanol were added to give a clear solution. After 0.5 hour, the solvents were removed by evaporation under an oil pump vacuum to give a gum which was partitioned between 30 ml of ethyl acetate and 20 ml of water. The white solid which formed was removed by filtration to give 0.64 g of crude product of melting point 179°-182° C. (decomposition). This crude product was stirred with methanol and then removed by filtration to give 0.48 g of pure 5'-azido-2',5'-dideoxy- 5-(2-chloroethyl)-uridine of melting point 197°-199° C. (decomposition).

後処理

  1. additionwere added
  2. customto give a solution within 5 minutes at room temperature
  3. customto give a hazy orange colored solution which
  4. customto give a clear solution
  5. waitAfter 0.5 hour
  6. customthe solvents were removed by evaporation under an oil pump vacuum
  7. customto give a gum which
  8. customwas partitioned between 30 ml of ethyl acetate and 20 ml of water
  9. customThe white solid which formed
  10. customwas removed by filtration
  11. customto give 0.64 g of crude product of melting point 179°-182° C. (decomposition)
  12. customremoved by filtration

出典と根拠

ORDレコード
ord-4ca87d5efd4d46d5bbe506021ac72059
出典データセット
uspto-grants-1991_04
特許番号
US05010060

関連ノート

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