L-Serine, methyl ester, hydrochloride (1:1) → HCID 90392794, compound

HRID 1479819Notes

Reaction equation

HRID 1479819 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[Cl:10][C:11]1[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=1>C(Cl)Cl>[Cl:10][C:11]1[S:15][C:14]([S:16]([NH:6][C@@H:5]([CH2:7][OH:8])[C:4]([O:3][CH3:2])=[O:9])(=[O:18])=[O:17])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 27339255-Chlorothiophene-2-sulfonyl chloride

Product 1

HCID 90392794HCID 90392794, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-Serine methyl ester hydrochloride (5 g, 32.13 mmol) dissolved in methylene chloride (200 ml) was added with TEA (2 equiv., 8.95 ml) and in one portion 5-chlorothiophene-2-sulfonyl chloride (1.0 equiv., 6.97 g). The reaction was refluxed for 4 hours. The solvent was evaporated and the crude was dissolved in AcOEt (100 ml) and washed with water (1×80 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by crystallization from diethyl ether and petroleum ether afforded 10 g of the white product. Yield=93% 1HNMR (DMSO, 200 MHz) δ 2.81 (2H, q, J=7.2 Hz), 3.52 (3H, s), 3.92 (1H, t), 5.06 (1H, bs), 7.24 (1H, dd, J=4.2 Hz), 7.45 (1H, dd, J=4 Hz), 8.92 (1H, bs)

Workup

  1. temperatureThe reaction was refluxed for 4 hours
  2. customThe solvent was evaporated
  3. dissolutionthe crude was dissolved in AcOEt (100 ml)
  4. washwashed with water (1×80 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude residue
  8. customby crystallization from diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-0d27cde77bec4c25ab2786e2e2b88fe2
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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