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Diisopropylethylamine → tert-butyl [(1S)-1-({[(1S)-1-benzyl-2-({(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}amino)-2-oxoethyl]amino}carbonyl)-3-phenylpropyl]carbamate

HRID 1182692
ノート
印刷プレビュー

反応式

HRID 1182692 の反応式
[NH2:1][C@@H:2]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:3]([NH:5][C@H:6]([B:12]1[O:16][C@@H:15]2[CH2:17][C@@H:18]3[CH2:21][C@H:20]([C@:14]2([CH3:24])[O:13]1)[C:19]3([CH3:23])[CH3:22])[CH2:7][CH:8]1[CH2:11][CH2:10][CH2:9]1)=[O:4].[CH3:32][C:33]([O:36][C:37]([NH:39][C@H:40]([C:49](O)=[O:50])[CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:38])([CH3:35])[CH3:34].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH2:25]([C@H:2]([NH:1][C:49]([C@@H:40]([NH:39][C:37](=[O:38])[O:36][C:33]([CH3:34])([CH3:32])[CH3:35])[CH2:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:50])[C:3]([NH:5][C@H:6]([B:12]1[O:16][C@@H:15]2[CH2:17][C@@H:18]3[CH2:21][C@H:20]([C@:14]2([CH3:24])[O:13]1)[C:19]3([CH3:23])[CH3:22])[CH2:7][CH:8]1[CH2:11][CH2:10][CH2:9]1)=[O:4])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acidHCID 68524856(2S)-2-amino-N-{(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}-3-phenylpropanamide

生成物 1

HCID 86725188
tert-butyl [(1S)-1-({[(1S)-1-benzyl-2-({(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}amino)-2-oxoethyl]amino}carbonyl)-3-phenylpropyl]carbamate
収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Into a 1-neck round-bottom flask was added (2S)-2-amino-N-{(1R)-2-cyclobutyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}-3-phenylpropanamide (217 mg, 0.511 mmol), Boc-homophe-OH (171 mg, 0.614 mmol), TBTU (246 mg, 0.767 mmol) and then N,N-dimethylformamide (14.5 mL, 0.187 mol) followed by N,N-diisopropylethylamine (0.187 mL, 1.07 mmol) dropwise at room temperature. The mixture was stirred at room temperature overnight The DMF was removed from the reaction mixture under vacuum and the resulting residue purified by preparative TLC in 40% EtOAc/Hexanes to give 298 mg (85% yield) of the desired product as a white solid.

後処理

  1. customwas removed from the reaction mixture under vacuum
  2. customthe resulting residue purified by preparative TLC in 40% EtOAc/Hexanes

出典と根拠

ORDレコード
ord-ac6a2e62e2ba4f21bbec627da60afbb6
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08664200B2

反応ノート

読み込み中…

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