Hydrochloric Acid → HCID 67630140, compound

HRID 275589Notes

Reaction equation

HRID 275589 reaction equation
[OH-].[Na+].[CH:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]([CH2:13][CH:14]([NH2:18])[C:15]([OH:17])=[O:16])=[O:12])=[CH:5][CH:4]=1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[S:29](Cl)(=[O:31])=[O:30].Cl>O1CCOCC1>[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[S:29]([NH:18][C@@H:14]([C:15]([OH:17])=[O:16])[CH2:13][C:11]([O:10][CH2:9][C:6]1[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=1)=[O:12])(=[O:30])=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 71252-Naphthalenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 3519812-amino-4-oxo-4-phenylmethoxybutanoic acid

Product 1

HCID 67630140HCID 67630140, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

22.4 ml of 2N NaOH are added dropwise at 10° C. to a 5 solution of 5 g of D-aspartic acid β-benzyl ester and 5.07 g of 2-naphthylsulphonyl chloride in 80 ml of dioxan cooled to 10° C. The reaction mixture is subsequently stirred at room temperature for 2 hours and then treated with 25 ml of 1N hydrochloric acid. After evaporation of the dioxan the residue is taken up in ethyl acetate and washed with water. After drying and evaporation of the ethyl acetate phase there are obtained 9.1 g of 4-benzyl 1-hydrogen N-(2-naphthylsulfonyl)-D-aspartate, Rf=0.53 (ethyl acetate/glacial acetic acid 0.97:0.03).

Workup

  1. customAfter evaporation of the dioxan the residue
  2. washwashed with water
  3. customAfter drying
  4. customevaporation of the ethyl acetate phase

Sources & evidence

ORD record
ord-60e4963ab30048499b335aac0e423186
Source dataset
uspto-grants-1995_02
Patent number
US05393760

Reaction notes

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