Hydrochloric Acid → (S)-2-amino-4-(methylthio)butane-1-sulfonic acid hydrochloride

HRID 2040502Notes

Reaction equation

HRID 2040502 reaction equation
C(OC([NH:8][C@@H:9]([CH2:15][CH2:16][S:17][CH3:18])[CH2:10][S:11]([O-:14])(=[O:13])=[O:12])=O)(C)(C)C.[Na+].[ClH:20]>O>[ClH:20].[NH2:8][C@@H:9]([CH2:15][CH2:16][S:17][CH3:18])[CH2:10][S:11]([OH:14])(=[O:12])=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86656460sodium (S)-2-(tert-butoxycarbonylamino)-4-(methylthio)butane-1-sulfonate

Product 1

HCID 86656462(S)-2-amino-4-(methylthio)butane-1-sulfonic acid hydrochlorideYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium (S)-2-(tert-butoxycarbonylamino)-4-(methylthio)butane-1-sulfonate (350 mg) was treated with 6 N HCl in water at 40° C. for 1 h. The reaction mixture was purified on Diaion HP-20 column eluting with water (200 mL), then 20% CH3CN in water. The fractions were concentrated and dried under vacuum to give (S)-2-amino-4-(methylthio)butane-1-sulfonic acid hydrochloride as a light yellow solid (53 mg, 21%). 1H NMR (DMSO-d6, 300 MHz) d 8.05 (br s, 3H, NH3), 3.4 (br s, 1H, NCH), 2.65 (m, 4H, SCH2 and OSCH2), 2.1 (s, 3H, SCH3), 1.8-2.1 (m, 2H, NCHCH2CH2SCH3). LC-MS: 0.15 min (eluted along with solvent peak); MS (ESI−) m/z 198 (M−1)+. Purity: >95% by 1H NMR and LC-MS. The chirality of the final product was based on the commercially available starting material, (S)-tert-butyl 1-hydroxy-4-(methylthio)butan-2-ylcarbamate, which has a natural configuration (L−). The reactions did not change the chiral center.

Workup

  1. customThe reaction mixture was purified on Diaion HP-20 column
  2. washeluting with water (200 mL)
  3. concentrationThe fractions were concentrated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-724c041852c847e99ad8509c4cd1ac7d
Source dataset
uspto-grants-2013_11
Patent number
US08580859B2

Reaction notes

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