Hydrochloric Acid → HCID 22397934, compound

HRID 433657Notes

Reaction equation

HRID 433657 reaction equation
O1CCCC1.C([O:8][C:9](=[O:40])[CH:10]([NH:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])[CH2:11][C:12]1[O:16][N:15]=[C:14]([CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[S:22]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=2)(=[O:24])=[O:23])[CH:13]=1)C.[OH-].[Li+].Cl>CO>[CH2:37]([O:36][C:34]([NH:33][CH:10]([CH2:11][C:12]1[O:16][N:15]=[C:14]([CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[S:22]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=2)(=[O:23])=[O:24])[CH:13]=1)[C:9]([OH:40])=[O:8])=[O:35])[CH:38]=[CH2:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 20610287HCID 20610287, compound

Product 1

HCID 22397934HCID 22397934, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A tetrahydrofuran (1.0 mL) and methanol (0.5 mL) solution of 2-allyloxycarbonylamino-3-{3-[1-(3,5-dichloro-benzenesulfonyl)-pyrrolidin-2-yl]-isoxazol-5-yl}-propionic acid ethyl ester (59 mg, 0.108 mmol) was stirred with 2M aqueous lithium hydroxide (0.5 mL) at room temperature for 40 minutes. The reaction was acidified to pH 1 with 1 M hydrochloric acid and extracted twice with ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated in vacuo to give the title compound as a white solid (51 mg, 91%). MS (CI) m/z 518 (M+1).

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c8d2f038738464abc90b52f6f9afd96
Source dataset
uspto-grants-2003_12
Patent number
US06667331B2

Reaction notes

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