2-Thiophenesulfonyl chloride → HCID 93038122, compound

HRID 1479871Notes

Reaction equation

HRID 1479871 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[OH:8][CH2:7][C@H:5]([NH:6][S:15]([C:11]1[S:10][CH:14]=[CH:13][CH:12]=1)(=[O:17])=[O:16])[C:4]([O:3][CH3:2])=[O:9]

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 93038122HCID 93038122, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of L-serine-methyl ester hydrochloride (3.0 g, 19.3 mmol) in CH2Cl2 (80 mL) was added with TEA (1.1 mol eq, 2.9 mL) and the mixture was stirred at r.t. for 10 minutes. Then 2-thiophen-sulphonyl chloride (1 mol eq, 3.52 g) and additional TEA (1.1 mol eq) were added and the solution hated at 60° C. overnight. The solvent was removed under reduced pressure, water was added to the residue (100 mL) and the aqueous phase extracted with EtOAc (3×40 mL). The recombined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 5H as white solid (4.9 g, 95% yield). 1HNMR (DMSO, 200 MHz) δ 3.61 (s, 2H), 3.82 (t, 2H, J=6.3), 4.14 (m, 1H), 4.62 (t, 1H), 5.25 (t, 1H), 7.21 (m, 1H), 7.75 (dd, 1H, J=2.1), 7.96 (dd, 1H, J=1.9), 8.23 (d, 1H).

Workup

  1. additionwas added with TEA (1.1 mol eq
  2. waitthe solution hated at 60° C. overnight
  3. customThe solvent was removed under reduced pressure, water
  4. additionwas added to the residue (100 mL)
  5. extractionthe aqueous phase extracted with EtOAc (3×40 mL)
  6. dry with materialThe recombined organic phases were dried over Na2SO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eed4dfac10514a7dbc31d95b92404f33
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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