Ethyl Acetate → HCID 86686429, 화합물

HRID 632579

반응식

HRID 632579 반응식
[Br:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:22]1([O:27][C:28](=[O:35])[C@H:29]([CH2:31][CH:32]([CH3:34])[CH3:33])[NH2:30])[CH2:26][CH2:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>ClC(Cl)C>[Br:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:30][C@H:29]([C:28]([O:27][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)=[O:35])[CH2:31][CH:32]([CH3:34])[CH3:33])=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 112064214-(Bromomethyl)benzaldehydeHCID 86633653L-leucine cyclopentyl ester tosylate

생성물 1

HCID 86686429HCID 86686429, 화합물수율 83.3%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 4-(bromomethyl)-benzaldehyde (0.940 g, 4.72 mmol) in dichloroethane (20 mL) was added L-leucine cyclopentyl ester tosylate (2.40 g, 6.4 mmol) and sodium triacetoxyborohydride (2.53 g, 11.9 mmol). The reaction mixture was stirred for 1 hour then poured into ethyl acetate (300 mL). The organic fraction was washed with saturated sodium hydrogen carbonate (100 mL, 3 times 50 mL) then dried (MgSO4), concentrated and purified by flash column chromatography (SiO2, gradient 0-3% methanol-dichloromethane) to yield the desired product (1.504 g, 83% yield). LC/MS: m/z 382/384 [M+H]+

후처리

  1. washThe organic fraction was washed with saturated sodium hydrogen carbonate (100 mL, 3 times 50 mL)
  2. dry with materialthen dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (SiO2, gradient 0-3% methanol-dichloromethane)

출처 및 근거

ORD 기록
ord-c2bbaaaceb69469db13001c6be58a8eb
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321718B2

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