Ethyl Acetate → 1-cyclopentyl N-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]-L-leucinate

HRID 632562

반응식

HRID 632562 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:25]1([O:30][C:31](=[O:38])[C@H:32]([CH2:34][CH:35]([CH3:37])[CH3:36])[NH2:33])[CH2:29][CH2:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>ClC(Cl)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:33][C@H:32]([C:31]([O:30][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)=[O:38])[CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86633653L-leucine cyclopentyl ester tosylate

생성물 1

HCID 866864161-cyclopentyl N-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]-L-leucinate

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of N-tert-butoxycarbonyl-3-pyrrolidinone (0.382 g, 4.76 mmol) in dichloroethane (20 mL) was added L-leucine cyclopentyl ester tosylate (1.96 g, 5.3 mmol) and sodium triacetoxyborohydride (2.65 g, 12.5 mmol). The mixture was stirred at room temperature for 3 hours, then poured into ethyl acetate (150 mL) and quenched with saturated ammonium chloride solution (50 mL) and washed with saturated sodium hydrogen carbonate solution (3 times 30 mL). The organic extracts were dried (MgSO4), concentrated and purified by flash column chromatography (7:3 ethyl acetate:heptane) to yield the desired product. LC/MS: m/z 369.25 [M+H]+

후처리

  1. customquenched with saturated ammonium chloride solution (50 mL)
  2. washwashed with saturated sodium hydrogen carbonate solution (3 times 30 mL)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (7:3 ethyl acetate:heptane)

출처 및 근거

ORD 기록
ord-6da453aad4f84aac847932ee8559d33c
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321718B2

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