Lithium borohydride → [(S)-1-(2-Hydroxy-1-pyridin-2-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

HRID 1040461노트

반응식

HRID 1040461 반응식
C[O:2][C:3](=O)[CH:4]([NH:11][C:12](=[O:23])[C@@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[Li+].[BH4-]>C1COCC1>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:13]([C:12](=[O:23])[NH:11][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[CH2:3][OH:2])[CH3:14])([CH3:20])([CH3:21])[CH3:22]

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 67390971HCID 67390971, 화합물

생성물 1

HCID 67389928[(S)-1-(2-Hydroxy-1-pyridin-2-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of ((S)-2-tert-Butoxycarbonylamino-propionylamino)-pyridin-2-yl-acetic acid methyl ester (1.12 g, 3.32 mmol) in 15 mL of THF was added LiBH4 (2 M in THF, 1.66 mL, 3.32 mmol) drop wise and the reaction was stirred at room temperature for 16 h. The reaction was carefully quenched by water, neutralized with 0.1 N HCl aq., extracted with EtOAc, washed with aq. NaHCO3 and Brine. Dried over Na2SO4, filtered and concentrated in vacuo to afford [(S)-1-(2-Hydroxy-1-pyridin-2-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (770 mg, 77%) as a white foam, m/z 310.60 [M+1]+

후처리

  1. customThe reaction was carefully quenched by water
  2. extractionextracted with EtOAc
  3. washwashed with aq. NaHCO3 and Brine
  4. dry with materialDried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-68f4059682a540188aca634e6e09ed4f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552205B2

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