Triethylamine → (S)-3-Methyl-2-((thianthren-2-ylsulfonyl)amino)butanoic acid

HRID 1953390노트

반응식

HRID 1953390 반응식
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:15](Cl)(=[O:17])=[O:16].C([O:23][C:24](=[O:30])[C@H:25]([CH:27]([CH3:29])[CH3:28])[NH2:26])(C)(C)C.C(N(CC)CC)C>ClCCl.FC(F)(F)C(O)=O>[CH3:28][CH:27]([CH3:29])[C@H:25]([NH:26][S:15]([C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:13][C:14]=2[CH:1]=1)(=[O:17])=[O:16])[C:24]([OH:30])=[O:23]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 114626tert-Butyl L-valinateHCID 15487617Thianthrene-2-sulfonyl chloride

생성물 1

HCID 15487604(S)-3-Methyl-2-((thianthren-2-ylsulfonyl)amino)butanoic acid수율 17.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

The crude thianthrene-2-sulfonyl chloride (1.19 g, 3.77 mmol) was mixed with 0.79 g (3.77 mmol) of (L)-valine-t-butyl ester and triethyl amine (1.58 mL, 11.3 mmol) in 50 mL of dichloromethane. After 2 hours, the reaction was partitioned between 1 M HCl and dichloromethane. The organic phase was washed with saturated sodium carbonate solution, dried over magnesium sulfate, and concentrated to give an oily green solid. This compound (0.46 g, 1.0 mmol) was stirred in 5 mL of trifluoroacetic acid for 1 hour and then concentrated in vacuo. The residue was triturated with diethyl ether to give 0.26 g of the title compound as a fluffy white solid.

후처리

  1. customthe reaction was partitioned between 1 M HCl and dichloromethane
  2. washThe organic phase was washed with saturated sodium carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oily green solid
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-19abb55778c740ce96c1c1ad47fdd337
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06117869

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