Allyl bromide → Rocuronium Bromide

HRID 329958

反応式

HRID 329958 の反応式
[CH2:1]([Br:4])[CH:2]=[CH2:3].[C:5]([O:8][C@H:9]1[C@@H:14]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:13][C@H:12]2[C@H:20]3[C@H:30]([CH2:31][CH2:32][C@:10]12[CH3:11])[C@:28]1([CH3:29])[C@H:23]([CH2:24][C@H:25]([OH:39])[C@@H:26]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH2:27]1)[CH2:22][CH2:21]3)(=[O:7])[CH3:6]>ClCCl>[Br-:4].[C:5]([O:8][C@H:9]1[C@@H:14]([N+:15]2([CH2:3][CH:2]=[CH2:1])[CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:13][C@H:12]2[C@H:20]3[C@H:30]([CH2:31][CH2:32][C@:10]12[CH3:11])[C@:28]1([CH3:29])[C@H:23]([CH2:24][C@H:25]([OH:39])[C@@H:26]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[CH2:27]1)[CH2:22][CH2:21]3)(=[O:7])[CH3:6]

参加物

4

反応物 2

HCID 7841Allyl bromideHCID 16064933(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

生成物 1

HCID 441351Rocuronium Bromide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-propenyl bromide (1.95 ml) was added to a solution of (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16(1-pyrrolidinyl)-androstane-3,17-diol 17-acetate (1.35 g) in dichloromethane (27 ml) and the solution was sealed in a pressure bottle at room temperature for 22 h. The solvent was removed under reduced pressure with the minimum of heating and the crude solid (1.59 g) was chromatographed on alumina (Fluka type 5016A). The pure fractions were combined, taken up in dichloromethane (15 ml) and diethyl ether (100 ml) was added to precipitate pure 1-[(2β,3α,5α,16β,17β)-17-acetyloxy-3-hydroxy-2-(4-morpholinyl)-androstan-16-yl]-1-(2propenyl)-pyrrolidinium bromide (1.14 g), m.p. 161°-169° C.; [α]D20 =+18.7° (c 1.03 in CHCl3).

後処理

  1. customthe solution was sealed in a pressure bottle at room temperature for 22 h
  2. customThe solvent was removed under reduced pressure with the minimum
  3. temperatureof heating
  4. customthe crude solid (1.59 g) was chromatographed on alumina (Fluka type 5016A)
  5. additiondiethyl ether (100 ml) was added
  6. customto precipitate pure 1-[(2β,3α,5α,16β,17β)-17-acetyloxy-3-hydroxy-2-(4-morpholinyl)-androstan-16-yl]-1-(2propenyl)-pyrrolidinium bromide (1.14 g), m.p. 161°-169° C.
  7. custom[α]D20 =+18.7° (c 1.03 in CHCl3)

出典と根拠

ORDレコード
ord-59c713a0ac23449fae6d5f1de6019272
出典データセット
uspto-grants-1990_01
特許番号
US04894369

関連ノート

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