Hydrochloric Acid → HCID 57820074, compound

HRID 1714159Notes

Reaction equation

HRID 1714159 reaction equation
C[O:2][C:3](=[O:31])[CH:4]([C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14](=[O:30])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:8][CH:7]=1)[OH:5].[OH-].[Li+].Cl>C1COCC1>[C:26]([O:25][C:23]([NH:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][C:14](/[CH:13]=[CH:12]/[C:9]1[CH:8]=[CH:7][C:6]([CH:4]([OH:5])[C:3]([OH:31])=[O:2])=[CH:11][CH:10]=1)=[O:30])=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59464431HCID 59464431, compound

Product 1

HCID 57820074HCID 57820074, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-hydroxy-acetic acid methyl ester (10.0 g, 23.5 mmol) in THF (100 mL) was added aqueous lithium hydroxide (1 M, 47 mL). After stirring at room temperature for 1 h, the pH was adjusted to 3 by addition of 0.5 N HCl. The resulting mixture was extracted with ethyl acetate (100 mL×2). The combined organics were washed with brine, dried over Na2SO4, and concentrated to afford the crude product as a pale-green solid (9.8 g, quantitative yield) which was used without further purification.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×2)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-10657901515f414aaddb732ea8a04597
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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