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 2282875ノート

反応式

HRID 2282875 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-09b43543dc2040d580b11f55bdaaf6cb
出典データセット
uspto-grants-2015_09
特許番号
US09138486B2

反応ノート

読み込み中…