Methanol → Methylnaltrexone Bromide

HRID 1798791ノート

反応式

HRID 1798791 の反応式
[CH3:1][N+:2]1([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]4[O:21][C@H:6]5[C:7]([CH2:9][CH2:10][C@:11]2([OH:22])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8].[Br-:27].[I-].CO>O>[CH3:1][N+:2]1([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]4[O:21][C@H:6]5[C:7]([CH2:9][CH2:10][C@:11]2([OH:22])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8].[Br-:27]

参加物

4

反応物 2

HCID 887MethanolHCID 131727973HCID 131727973、化合物

生成物 1

HCID 5361917Methylnaltrexone Bromide

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

The foam (4) (597 mg) was dispersed in water (6 ml)/methanol (2 ml). Some dark oil remained undissolved. The clear supernatant liquid was decanted and applied to the prepared anion exchange resin column. The residue was washed twice with methanol (0.2 ml)/water (3 ml). The supernatant liquors were applied to the column. The column was eluted with 4.2 L of sterile water and fractions of ˜20 ml were collected. The presence of N-Methylnaltrexone salt was detected by liquid chromatography/mass spectrometry (LC/MS). The majority of N-Methylnaltrexone was located in the initial 1.5 L of eluate of which the first 600 ml contained the most pure material by TLC (4:1 dichloromethane/methanol, normal phase silica). The first 600 ml of eluate was combined and concentrated on the rotary evaporator to give a whitish glass. The water bath was maintained at ˜35° C. Care was needed to control foaming of the eluate while evaporating.

後処理

  1. customThe clear supernatant liquid was decanted
  2. washThe residue was washed twice with methanol (0.2 ml)/water (3 ml)
  3. washThe column was eluted with 4.2 L of sterile water and fractions of ˜20 ml
  4. customwere collected
  5. concentrationconcentrated on the rotary evaporator
  6. customto give a whitish glass
  7. customwhile evaporating

出典と根拠

ORDレコード
ord-6037a356ef1446788f013af825f97ea9
出典データセット
uspto-grants-2013_01
特許番号
US08343992B2

反応ノート

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