Sulfuric Acid → (S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

HRID 36645

반응식

HRID 36645 반응식
[C:1]1([S:7]([NH:10][C@@H:11]([CH2:15][NH2:16])[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[CH3:22][C:23](=[CH2:25])[CH3:24].[ClH:26].CCOCC>C(Cl)(Cl)Cl.COCCOC>[ClH:26].[C:1]1([S:7]([NH:10][C@@H:11]([CH2:15][NH2:16])[C:12]([O:14][C:23]([CH3:25])([CH3:24])[CH3:22])=[O:13])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 10752796(2S)-3-amino-2-(benzenesulfonamido)propanoic AcidHCID 10953452Ether hydrochloride

생성물 1

HCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
-78 °C

실험 절차

In a Fischer-Porter tube, a mixture of 22-2 (102 g, 42 mmol) and DME (150 mL) was sequentially treated with H2SO4 (6.4 mL, 0.12 mol), cooled to -78° C., and then condensed isobutylene (75 mL). The cooling bath removed. After 2 h, ice-water (250 mL) was added followed by washing with ether (2×). The aqueous phase was basified with aq 5N NaOH, then saturated with NaCl, followed by extraction with EtOAc (3×). The combined extracts were washed with brine dried (MgSO4), and concentrated to give a white solid. This was dissolved in CHCl3 then treated with 1N HCl/ether (22 mL) then concentrated to give 22-3 as a glossy yellow solid.

후처리

  1. customThe cooling bath removed
  2. additionice-water (250 mL) was added
  3. washby washing with ether (2×)
  4. extractionsaturated with NaCl, followed by extraction with EtOAc (3×)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a white solid
  9. concentrationthen concentrated

출처 및 근거

ORD 기록
ord-b0d0a3512ec748a0a355906b81a46fe3
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416099

연결된 노트

불러오는 중…