THF diethylamine → N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

HRID 74787ノート

反応式

HRID 74787 の反応式
C1C2C(COC([NH:18][C@H:19]([C:23]([N:25]([C@@H:27]([C@@H:57]([CH3:60])[CH2:58][CH3:59])[C@H:28]([O:55][CH3:56])[CH2:29][C:30]([N:32]3[CH2:36][CH2:35][CH2:34][C@H:33]3[C@H:37]([O:53][CH3:54])[C@@H:38]([CH3:52])[C:39]([NH:41][C@H:42]([CH3:51])[C@@H:43]([OH:50])[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:40])=[O:31])[CH3:26])=[O:24])[CH:20]([CH3:22])[CH3:21])=O)C3C(=CC=CC=3)C=2C=CC=1.C1COCC1.C(NCC)C>>[OH:50][C@@H:43]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C@H:42]([NH:41][C:39](=[O:40])[C@H:38]([CH3:52])[C@H:37]([C@@H:33]1[CH2:34][CH2:35][CH2:36][N:32]1[C:30](=[O:31])[CH2:29][C@@H:28]([O:55][CH3:56])[C@@H:27]([N:25]([CH3:26])[C:23](=[O:24])[C@H:19]([CH:20]([CH3:21])[CH3:22])[NH2:18])[C@@H:57]([CH3:60])[CH2:58][CH3:59])[O:53][CH3:54])[CH3:51]

参加物

3

反応物 2

HCID 19023656THF diethylamineHCID 89582415N~2~-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

生成物 1

HCID 89573130N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide収率 43.2%

実験手順

To a stirring solution of #132 (1.33 g, 1.60 mmol, 1.0 eq) in 10 mL of THF diethylamine (5 mL, 50 mM, 31.3 eq) was added. The reaction was allowed to stir at room temperature for 4 hours. Reaction was concentrated in vacuo and the residue was purified by silica chromatography (Gradient: 0%-30% methanol in ethyl acetate) producing #133 (418 mg, 43%) as a white solid. LC-MS (Protocol Q1): m/z 605.2 [M+H+] retention time=1.48 minutes.

後処理

  1. customReaction
  2. concentrationwas concentrated in vacuo
  3. customthe residue was purified by silica chromatography (Gradient: 0%-30% methanol in ethyl acetate)

出典と根拠

ORDレコード
ord-1bdd3b53cc8848da973467386c9c0b65
出典データセット
uspto-grants-2014_09
特許番号
US08828401B2

反応ノート

読み込み中…