Hydrochloric Acid → 3-(naphthalene-2-sulfonamido)-3-phenylpropionic Acid

HRID 1371530Notes

Reaction equation

HRID 1371530 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[S:23](Cl)(=[O:25])=[O:24].O.Cl>O1CCOCC1.[OH-].[Na+]>[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[S:23]([NH:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5])(=[O:24])=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 71252-Naphthalenesulfonyl chlorideHCID 69189DL-beta-Phenylalanine

Product 1

HCID 36326413-(naphthalene-2-sulfonamido)-3-phenylpropionic AcidYield 83.5%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

4.13 g of 3-amino-3-phenylpropionic acid are dissolved in a mixture of 100 ml of dioxane and 25 ml of 1N NaOH, 5.6 g of 2-naphthalenesulphonyl chloride are added portionwise while maintaining a pH of 10.5–10.8 by addition of 1N NaOH, and the mixture is stirred for 2 hours at RT. The reaction mixture is diluted by adding 400 ml of water, acidified to pH 2 by adding 2N HCl, and extracted with EtOAc, the organic phase is washed with KHSO4/K2SO4 buffer solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. 7.33 g of the expected product are obtained after triturating in heptane and drying under vacuum; m.p.=126–129° C.

Workup

  1. additionare added portionwise
  2. temperaturewhile maintaining a pH of 10.5–10.8
  3. additionThe reaction mixture is diluted
  4. extractionextracted with EtOAc
  5. washthe organic phase is washed with KHSO4/K2SO4 buffer solution
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-f1867a433aa04e598aa9b087ee0d8ad3
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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