2-Mesitylenesulfonyl chloride → 3-tert-Butoxycarbonylamino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester

HRID 650668노트

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HRID 650668 반응식
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH2:14])[CH2:5][NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:16]1([CH3:28])[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[S:24](Cl)(=[O:26])=[O:25].CCN(C(C)C)C(C)C>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:14][S:24]([C:17]1[C:18]([CH3:23])=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=1[CH3:28])(=[O:26])=[O:25])[CH2:5][NH:6][C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8]

참가 물질

6

반응물 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 3442239Methyl 2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

생성물 1

HCID 220066833-tert-Butoxycarbonylamino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester수율 91.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A mixture of 3-tert-Butoxycarbonylamino-2-aminopropionic acid methyl ester (3.5 g, 13.7 mmol), mesitylsulfonyl chloride (3.9 g, 17.8 mmol), DIEA (7.2 mL, 41.1 mmol) in dichloromethane (100 mL) was stirred at 0° C. for one hour and overnight at room temperature. The solvent was removed and the crude reaction product was taken up in ethyl acetate (340 mL). The solution was washed with 5% solution of sodium carbonate (30 mL), 5% solution of hydrochloric acid (30 mL), with saturated sodium chloride solution (30 mL). Solvent was than dried over sodium sulfate and evaporated. Purification of the residue on silica gel (10%MeOH-EtOAc) gave 5.00 g of pure compound O-1 (84% yield).

후처리

  1. customThe solvent was removed
  2. customthe crude reaction product
  3. washThe solution was washed with 5% solution of sodium carbonate (30 mL), 5% solution of hydrochloric acid (30 mL), with saturated sodium chloride solution (30 mL)
  4. dry with materialthan dried over sodium sulfate
  5. customevaporated
  6. customPurification of the residue on silica gel (10%MeOH-EtOAc)

출처 및 근거

ORD 기록
ord-1e9bfc59ac1f4141a3284f99a1723b56
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274620B1

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