Chloroacetaldehyde → 2-[Benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester

HRID 408577

反応式

HRID 408577 の反応式
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].[Cl:22][CH2:23][CH:24]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:24][CH2:23][Cl:22])[CH3:6])[CH3:2]

参加物

7

反応物 5

HCID 33ChloroacetaldehydeHCID 176Acetic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 222273Ethyl 2-(benzylamino)propanoateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 705577792-[Benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

To a solution of 2-benzylamino-propionic acid ethyl ester (1 eq.) in dry DCM was added MgSO4 (0.75 eq.). The reaction was cooled to 0° C. then the above solution of chloroacetaldehyde in dry DCM (solution I) and acetic acid (1 eq.) were added. Sodium triacetoxyborohydride (1.5 eq.) was added portionwise. The reaction was stirred for 1 h at 0° C. The crude was carefully quenched with a saturated aqueous solution of NaHCO3. Then aqueous NaOH (2N) was added. The aqueous layer was extracted with DCM. The combined organic layers were washed with an aqueous saturated solution of NaHCO3, then dried over MgSO4 and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc 98/2 to 95/5) to afford 2-[benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester.

後処理

  1. customThe crude was carefully quenched with a saturated aqueous solution of NaHCO3
  2. additionThen aqueous NaOH (2N) was added
  3. extractionThe aqueous layer was extracted with DCM
  4. washThe combined organic layers were washed with an aqueous saturated solution of NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc 98/2 to 95/5)

出典と根拠

ORDレコード
ord-ebec0e38facf4fb582b154836ae73339
出典データセット
uspto-grants-2014_06
特許番号
US08759334B2

関連ノート

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