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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
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HRID 2301765 반응식
[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]
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-342bc66a2a1b4404b06a114fc2f7ff2f
출처 데이터셋
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06500844B1

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