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

HRID 1953390Notes

Reaction equation

HRID 1953390 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-19abb55778c740ce96c1c1ad47fdd337
Source dataset
uspto-grants-2000_09
Patent number
US06117869

Reaction notes

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