Sodium Carbonate → HCID 22397934, compound

HRID 1071273Notes

Reaction equation

HRID 1071273 reaction equation
Cl.C([O:4][C:5](=[O:25])[CH:6]([NH:18][C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH2:7][C:8]1[O:12][N:11]=[C:10]([CH:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)[CH:9]=1)C.C(=O)([O-])[O-].[Na+].[Na+].[Cl:32][C:33]1[CH:34]=[C:35]([S:40](Cl)(=[O:42])=[O:41])[CH:36]=[C:37]([Cl:39])[CH:38]=1>O>[CH2:22]([O:21][C:19]([NH:18][CH:6]([CH2:7][C:8]1[O:12][N:11]=[C:10]([CH:13]2[CH2:17][CH2:16][CH2:15][N:14]2[S:40]([C:35]2[CH:34]=[C:33]([Cl:32])[CH:38]=[C:37]([Cl:39])[CH:36]=2)(=[O:42])=[O:41])[CH:9]=1)[C:5]([OH:4])=[O:25])=[O:20])[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 69735596HCID 69735596, compound

Product 1

HCID 22397934HCID 22397934, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Allyloxycarbonylamino-3-(3-pyrrolidin-2-yl-isoxazol-5-yl)-propionic acid ethyl ester hydrochloride (110 mg, 0.294 mmol) and sodium carbonate (93.5 mg, 0.882 mmol) were dissolved in water (1.5 mL) and 3,5-dichlorobenzenesulfonylchloride (86.7 mg, 0.353 mmol) was added. This mixture was stirred overnight. The reaction was extracted twice with dichloromethane. The combined organic portion was washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield the title compound (59 mg, 37%). MS (Cl) m/z 545.7 (M+1) C. 2-Allyloxycarbonylamino-3-(3-pyrrolidin-2-yl-isoxazol-5-yl)-propionic acid ethyl ester hydrochloride

Workup

  1. extractionThe reaction was extracted twice with dichloromethane
  2. washThe combined organic portion was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe11f7654b7f4edca1e2bb3fc7c22c37
Source dataset
uspto-grants-2005_06
Patent number
US06903128B2

Reaction notes

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