Water → Boc-beta-chloro-ala-oh

HRID 1089998Notes

Reaction equation

HRID 1089998 reaction equation
[Cl:1][CH2:2][C@@H:3]([C:5]([OH:7])=[O:6])[NH2:4].C(N(CC)CC)C.[C:15]([O:19][C:20](ON=C(C1C=CC=CC=1)C#N)=[O:21])([CH3:18])([CH3:17])[CH3:16].O>O1CCOCC1>[C:15]([O:19][C:20]([NH:4][C@H:3]([C:5]([OH:7])=[O:6])[CH2:2][Cl:1])=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 4397723-chloro-L-alanine

Product 1

HCID 7020770Boc-beta-chloro-ala-ohYield 47.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.0 g (6.25 mmol) of 3-chloro-L-alanine and 1.3 mL of triethylamine in 50% aqueous 1,4-dioxane were added 1.69 g (6.90 mmol) of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile with stirring at room temperature. After 2 hours, the reaction mixture was poured into 20 mL of water and extracted twice with ethyl acetate. The organic layer was washed twice with water and then with saturated brine, dried over anhydrous magnesium sulfate and evaporated to give 0.66 g (40.5%) of white solid. Recrystallization from a mixture of ethyl acetate and n-hexane afforded 0.58 g of the pure product (35.6%) melting at 123°-124° C., with decomposition, and having the structural formula: ##STR75## The identity of the product was confirmed by IR and NMR analyses.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer was washed twice with water
  3. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-f6bbc24950e443c6adcf7f30c9bf226b
Source dataset
uspto-grants-1992_01
Patent number
US05079366

Reaction notes

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