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

HRID 1379685Notes

Reaction equation

HRID 1379685 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-5ed39ed144994029b97993206fad071f
Source dataset
uspto-grants-1997_09
Patent number
US05672599

Reaction notes

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