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Diisopropylethylamine → 1-(SR)-((t-Butoxycarbonyl)amino)-3-(SR)-((4-(N-(4-nitrobenzyloxycarbonyl)-N-(allyl)amino)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentane

HRID 2301765
ノート
印刷プレビュー

反応式

HRID 2301765 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH:20]=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[N+:23]([C:26]1[CH:45]=[CH:44][C:29]([CH2:30][O:31][C:32]([N:34]([CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:35][CH:36]=[CH2:37])=[O:33])=[CH:28][CH:27]=1)([O-:25])=[O:24].CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][N:41]2[CH2:42][CH2:43][CH:38]([N:34]([C:32]([O:31][CH2:30][C:29]3[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:45][CH:44]=3)=[O:33])[CH2:35][CH:36]=[CH2:37])[CH2:39][CH2:40]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18187642(SR)-((t-butoxycarbonyl)amino)-3-(SR)-(formyl)-4-(SR)-phenylcyclopentaneHCID 181876754-(N-(4-nitrobenzyloxycarbonyl)(N-allyl)amino)piperidine hydrochloride

生成物 1

HCID 181876031-(SR)-((t-Butoxycarbonyl)amino)-3-(SR)-((4-(N-(4-nitrobenzyloxycarbonyl)-N-(allyl)amino)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentane
収率 101.2%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-((SR)-((t-butoxycarbonyl)amino)-3-(SR)-(formyl)-4-(SR)-phenylcyclopentane (from Step G, derived from Higher Rf isomer in Step E) (30 mg, 0.11 mmol) in 1,2-dichloroethane (3 mL) was added 4-(N-(4-nitrobenzyloxycarbonyl)(N-allyl)amino)piperidine hydrochloride (45 mg, 0.126 mmol) and DIPEA (0.022 mL, 0.126 mmol). After 15 min, sodium triacetoxyborohydride (45 mg, 0.22 mmol) was added and the reaction was stirred at RT for 6 h. The reaction was diluted with methylene chloride, quenched with aq. sodium carbonate and extracted 3 times with methylene chloride. The organic layers were each washed with brine, dried over sodium sulfate, combined and concentrated in vacuo. The residue was purified by Prep TLC eluting with 5% methanol in methylene chloride to give the title product (66 mg) as the free amine.

後処理

  1. customquenched with aq. sodium carbonate
  2. extractionextracted 3 times with methylene chloride
  3. washeach washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Prep TLC
  7. washeluting with 5% methanol in methylene chloride

出典と根拠

ORDレコード
ord-342bc66a2a1b4404b06a114fc2f7ff2f
出典データセット
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06500844B1

反応ノート

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