2-Naphthalenesulfonyl chloride → 3-(naphthalene-2-sulfonamido)-3-phenylpropionic Acid

HRID 850012Notes

Reaction equation

HRID 850012 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].[OH-].[Na+].[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[S:25](Cl)(=[O:27])=[O:26]>O1CCOCC1.O.Cl>[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[S:25]([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:26])=[O:27]

Participants

7

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 14798Sodium Hydroxide2×HCID 69189DL-beta-Phenylalanine

Product 1

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

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4.13 g of 3-amino-3-phenylpropionic acid are dissolved in 100 ml of dioxane and 25 ml of 1N sodium hydroxide and 5.6 g of 2-naphthalenesulphonyl chloride are added portionwise, while maintaining the pH at 10.5-11 by addition of 1N sodium hydroxide. After stirring for 2 hours at RT, the mixture is diluted with 400 ml of water and 2N HCl is added in order to obtain pH=2. This mixture is extracted with EtOAc and the extracts are washed with a KHSO4 /K2SO4 buffer, dried over Na2SO4 and evaporated to dryness. The residue is triturated from heptane and the product is isolated by decanting and is then dried under vacuum. 7.33 g of the expected product are obtained, m.p.=126-129° C.

Workup

  1. temperaturewhile maintaining the pH at 10.5-11
  2. additionis added in order
  3. customto obtain pH=2
  4. extractionThis mixture is extracted with EtOAc
  5. washthe extracts are washed with a KHSO4 /K2SO4 buffer
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue is triturated from heptane
  9. customthe product is isolated
  10. customby decanting
  11. customis then dried under vacuum

Sources & evidence

ORD record
ord-c592f28d30fb4fa98384fb0c67fbeea1
Source dataset
uspto-grants-2000_01
Patent number
US06015812

Reaction notes

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