4-Methylmorpholine → N2-[(benzyloxy)carbonyl]-N1-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl)-3-[(1-propylbutyl)sulfonyl]alaninamide

HRID 857267ノート

反応式

HRID 857267 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([OH:26])=O)[CH2:13][S:14]([CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])(=[O:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[NH2:29][C@@H:30]([CH2:44][C:45]1[CH:50]=[C:49]([F:51])[CH:48]=[C:47]([F:52])[CH:46]=1)[C@H:31]([OH:43])[CH2:32][NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][CH3:42])[CH:36]=1.CN1CCOCC1.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:29][C@@H:30]([CH2:44][C:45]1[CH:46]=[C:47]([F:52])[CH:48]=[C:49]([F:51])[CH:50]=1)[C@H:31]([OH:43])[CH2:32][NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][CH3:42])[CH:36]=1)=[O:26])[CH2:13][S:14]([CH:17]([CH2:18][CH2:19][CH3:20])[CH2:21][CH2:22][CH3:23])(=[O:15])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57487281(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochlorideHCID 57508140N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl)alanineHCID 178418300HCID 178418300、化合物

生成物 1

HCID 58759847N2-[(benzyloxy)carbonyl]-N1-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl)-3-[(1-propylbutyl)sulfonyl]alaninamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl]alanine (LXXXIV, 4.0 g, 10 mmole) and (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochloride (1.2 g, 12 mmole) are mixed in anhydrous methylene chloride (50 ml). To the reaction mixture is added NMM (5.6 ml, 51 mmole), hydroxybenzotriazole (1.7 g, 13 mmole) and lastly 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.1 g (16 mmole). After stirring at 20–25° for 3 hours, HPLC analysis indicates complete reaction. The reaction mixture is diluted with methylene chloride and washed with saturated sodium bicarbonate solution, citric acid (0.5 M), and saline. The organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure to give N2-[(benzyloxy)carbonyl]-N1-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-3-[(1-propylbutyl)sulfonyl]alaninamide (LXXXV).

後処理

  1. customreaction
  2. washwashed with saturated sodium bicarbonate solution, citric acid (0.5 M), and saline
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f6b64d8d8f65409c9a99009b074ebfea
出典データセット
uspto-grants-2006_12
特許番号
US07144897B2

反応ノート

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