Hydrochloric Acid → (R)-2-Amino-3-(thiazol-4-YL)propanoic acid

HRID 1720991Notes

Reaction equation

HRID 1720991 reaction equation
Cl.CC(C)(OC([NH:8][C@H:9]([CH2:13][C:14]1[N:15]=[CH:16][S:17][CH:18]=1)[C:10]([OH:12])=[O:11])=O)C>O1CCOCC1>[NH2:8][C@H:9]([CH2:13][C:14]1[N:15]=[CH:16][S:17][CH:18]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 7020917Boc-D-4-Thiazolylalanine

Product 1

HCID 7020912(R)-2-Amino-3-(thiazol-4-YL)propanoic acidYield 74.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4N hydrochloric acid in dioxane (10 ml) was added to a solution of (R)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(4-thiazolyl)propanoic acid (2.0 g, 7.3 mmol) in dioxane (2 ml). The reaction mixture was stirred at room temperature for 3 hours, concentrated in vacuo and the residue was dissolved in water (3 ml). The pH was adjusted to 6.5 with 1N sodium hydroxide and this solution was passed through 20 ml of Dowex® AG50(H+). The column was eluted with water (250 ml) followed by 2% pyridine in water (300 ml). The product containing fractions were concentrated in vacuo to yield 0.94 g of title product.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was dissolved in water (3 ml)
  3. washThe column was eluted with water (250 ml)
  4. additionThe product containing fractions
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-462f6b0cad4d4264a377d0862190e7ed
Source dataset
uspto-grants-1996_04
Patent number
US05508272

Reaction notes

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