Hydrochloric Acid → HCID 22645033, compound

HRID 2414561Notes

Reaction equation

HRID 2414561 reaction equation
C[O:2][C:3](=[O:22])[C@H:4]([N:6]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]#[C:20][CH3:21])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:7])[CH3:5].O.[OH-].[Li+].Cl>C1COCC1.CO>[CH2:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([S:8]([N:6]([CH3:7])[CH:4]([CH3:5])[C:3]([OH:22])=[O:2])(=[O:9])=[O:10])=[CH:16][CH:15]=1)[C:19]#[C:20][CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 54154902HCID 54154902, compound

Product 1

HCID 22645033HCID 22645033, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 0.273 g (0.840 mmol) of (2R)-2-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-propionic acid methyl ester in 6 mL of THF/methanol (1/1) was added 0.123 g (2.94 mmol) of lithium hydroxide monohydrate and the resulting solution was stirred at room temperature for 3 h. The reaction was then acidified with 5% HCl solution and extracted with chloroform. The combined organics were dried over MgSO4, filtered and concentrated in vacuo to give 0.256 g of 2-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-propionic acid as a white solid. Electrospray Mass Spec 310.2 (M−H)−

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62842f8e092641339e8e21304828d626
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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