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

HRID 36645

反応式

HRID 36645 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b0d0a3512ec748a0a355906b81a46fe3
出典データセット
uspto-grants-1995_05
特許番号
US05416099

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