Dimethylformamide → 1-Adamantanecarbonyl chloride

HRID 862165

反応式

HRID 862165 の反応式
[CH2:1]1[CH2:11][CH2:10]N2[C:4](=NCCC2)[CH2:3][CH2:2]1.C1N=[C:16](N)[C:15]2N=CN(CCOCP(O)(O)=O)[C:14]=2N=1.[C:30]12([C:40]([O:42][CH2:43][Cl:44])=[O:41])[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2.[CH3:45]N(C=O)C>>[C:30]12([C:40]([O:42][CH2:43][Cl:44])=[O:41])[CH2:39][CH:34]3[CH2:33][CH:32]([CH2:38][CH:36]([CH2:35]3)[CH2:37]1)[CH2:31]2.[C:11]12([C:43]([Cl:44])=[O:42])[CH2:10][CH:4]3[CH2:3][CH:2]([CH2:14][CH:15]([CH2:16]3)[CH2:45]1)[CH2:1]2

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 60172AdefovirHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14699931Adamantoyl oxymethyl chloride

生成物 2

HCID 989151-Adamantanecarbonyl chlorideHCID 14699931Adamantoyl oxymethyl chloride

実験手順

DBU (1,8-diazabicyclo[5.4.0]undec-7-ene; 1.53 g, 10 mmol) was added to a suspension of PMEA (1.365 g, 5 mmol) in DMF (25 mL). Adamantoyl oxymethyl chloride (5.72 g, 25 mmol) in DMF (25 mL) was added to the reaction mixture which was then stirred for four days at room temperature and the volatiles were removed under vacuum. The crude product obtained after removal of the solvent was loaded onto a silica gel column and washed with 3% MeOH/CH2Cl2 to remove nonpolar impurities. 1 g (30%) of bis(adamantoyl oxymethyl)PMEA ester was eluted in 8% MeOH/CH2 Cl2. Adamantoyl oxymethyl chloride was obtained by conversion of 1-adamantanecarbonyl chloride (Aldrich No. 11,772-2) with (CH2 O)n /ZnCl2 and has been described (Bodor, et al J Med Chem (1980) 23:474-480).

後処理

  1. customthe volatiles were removed under vacuum
  2. customThe crude product obtained
  3. customafter removal of the solvent
  4. washwashed with 3% MeOH/CH2Cl2
  5. customto remove nonpolar impurities
  6. wash1 g (30%) of bis(adamantoyl oxymethyl)PMEA ester was eluted in 8% MeOH/CH2 Cl2

出典と根拠

ORDレコード
ord-a8a50f05b32742388077fbcfb5a298d8
出典データセット
uspto-grants-1998_02
特許番号
US05717095

関連ノート

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