Hydrochloric Acid → HCID 86629875, compound

HRID 2043924Notes

Reaction equation

HRID 2043924 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.[C:11]([NH:14][C:15]1[S:16][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:18][N:19]=1)(=[O:13])[CH3:12].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.O>[CH3:2][O:3][C:4]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[S:20]([C:17]1[S:16][C:15]([NH:14][C:11](=[O:13])[CH3:12])=[N:19][CH:18]=1)(=[O:21])=[O:22])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 3502612-Acetamido-1,3-thiazole-5-sulfonyl chlorideHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 86629875HCID 86629875, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of L-proline methylester hydrochloride (15 mmol), 2-acetylamino-thiazole-5-sulfonyl chloride (12 mmol) (prepared as described in J. Am. Chem. Soc 69, 2063, 1947), DIPEA (35 mmol) in DCM (50 mL) was stirred at room temperature over night. Addition of water and 1N HCl to pH 2. Isolation of the organic phase which was washed with water and brine, dried and concentrated to give (S)-1-(2-acetylamino-thiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as brown crystals. These were suspended in EtOH (15 mL) and added 4N HCl in dioxane (15 mL) and heated for 3H at 80° C. and then cooled to room temperature. Addition of aqueous NaHCO3 to neutral pH. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo to give (S)-1-(2-amino-thiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as colourless crystals.

Workup

  1. washIsolation of the organic phase which was washed with water and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-de5f3bce22f446d381690c3d291ea6a1
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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