Ethyl Acetate → HCID 86686429、化合物

HRID 632579ノート

反応式

HRID 632579 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 86686429HCID 86686429、化合物収率 83.3%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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]+

後処理

  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)

出典と根拠

ORDレコード
ord-c2bbaaaceb69469db13001c6be58a8eb
出典データセット
uspto-grants-2016_04
特許番号
US09321718B2

反応ノート

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