Hydrochloric Acid → HCID 67953291, compound

HRID 469716Notes

Reaction equation

HRID 469716 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[O:19]=[S:20]1(=[O:29])[CH2:25][CH2:24][N:23]([C:26](Cl)=[O:27])[CH2:22][CH2:21]1.C(N(CC)C(C)C)(C)C>O1CCCC1.C(OCC)(=O)C>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:26]([N:23]2[CH2:24][CH2:25][S:20](=[O:29])(=[O:19])[CH2:21][CH2:22]2)=[O:27])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 216949071,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl chlorideHCID 67455816(S)-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Product 1

HCID 67953291HCID 67953291, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (0.092 g; 0.337 mmol) in tetrahydrofuran (2.5 mL) is added 1,1-dioxo-1λ6-thiomorpholine-4-carbonyl chloride (0.067 g; 0.337 mmol) and N,N-diisopropylethylamine (0.123 mL; 0.708 mmol). The mixture is stirred at room temperature for 3 hours before diluting with ethyl acetate and washing with 1N hydrochloric acid and brine. The organics are concentrated in vacuo and purified by preparatory HPLC. The product fractions are pooled and concentrated in vacuo to afford title compound. ESI m/z 399 [M+H]+/397 [M−H]−

Workup

  1. washwashing with 1N hydrochloric acid and brine
  2. concentrationThe organics are concentrated in vacuo
  3. custompurified by preparatory HPLC
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9e89881f0614e31b0385fe2d482e5a1
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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