Hydrochloric Acid → HCID 86629875, compound

HRID 1363740Notes

Reaction equation

HRID 1363740 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-2d2897d3e08c4ba4a7f504a798b4c932
Source dataset
uspto-grants-2011_02
Patent number
US07884210B2

Reaction notes

Loading…