Hydrochloric Acid → (S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid

HRID 714129

반응식

HRID 714129 반응식
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].Cl[C:19]([O:21][CH3:22])=[O:20].Cl>C1COCC1>[CH3:22][O:21][C:19]([NH:12][C@H:8]([C:9]([OH:11])=[O:10])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:20]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 6586Methyl chloroformateHCID 516892Sodium Bicarbonate

생성물 1

HCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid수율 198.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A suspension of L-diphenylalanine (13.87 g, 57.5 mmol) in THF (100 ml), and saturated NaHCO3 (3 mL) stirred at 0° C. was treated with neat methyl chloroformate (11.81 g, 125 mmol) (slow addition), stirred at the same temperature for 10 min and then at room temperature for 14 h, made acidic by addition of 1M HCl and extracted with DCM, dried over MgSO4 filtered and concentrated to give title compound (17.1 g, 99% yield) as white solid. Used without further purification. MS: m/z=322.1 (MNa+).

후처리

  1. stirringstirred at the same temperature for 10 min
  2. extractionextracted with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1920437b70054c55954a76cd97adb72e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187415B2

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