Sodium triacetoxyborohydride → 1-cyclopentyl N-[2-(2-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)ethyl]-L-leucinate

HRID 632573

반응식

HRID 632573 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH2:37][CH:38]=O)[CH:34]=2)[CH2:29]1)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:51]1([O:56][C:57](=[O:64])[C@H:58]([CH2:60][CH:61]([CH3:63])[CH3:62])[NH2:59])[CH2:55][CH2:54][CH2:53][CH2:52]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH2:37][CH2:38][NH:59][C@H:58]([C:57]([O:56][CH:51]3[CH2:52][CH2:53][CH2:54][CH2:55]3)=[O:64])[CH2:60][CH:61]([CH3:62])[CH3:63])[CH:34]=2)[CH2:29]1)=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 86633653L-leucine cyclopentyl ester tosylateHCID 866864242-(2-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)acetaldehyde

생성물 1

HCID 866864231-cyclopentyl N-[2-(2-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)ethyl]-L-leucinate수율 53%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of Intermediate F (0.165 g, 0.32 mmol) in dichloroethane (10 mL) was added L-leucine cyclopentyl ester tosylate (0.197 g, 0.52 mmol) and sodium triacetoxyborohydride (0.151 g, 0.71 mmol). The mixture was stirred for 90 minutes, then quenched by addition of saturated ammonium chloride (20 mL). The product was extracted with dichloromethane (3 times 100 mL) and the combined organic extracts were dried (MgSO4), concentrated and purified by flash column chromatography (SiO2, ethyl acetate) to yield the desired product (0.089 g, 53% yield). LC/MS: m/z 701.25 [M+H]+

후처리

  1. customquenched by addition of saturated ammonium chloride (20 mL)
  2. extractionThe product was extracted with dichloromethane (3 times 100 mL)
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (SiO2, ethyl acetate)

출처 및 근거

ORD 기록
ord-c2cce7aaefb247978e051ebe20dbf00b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321718B2

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