Hydrochloric Acid → 2-(2-Amino-thiazol-5-ylmethyl)-malonic acid diethyl ester

HRID 1789930Notes

Reaction equation

HRID 1789930 reaction equation
[BH3-]C#N.[Na+].[CH2:5]([O:7][C:8](=[O:22])[C:9](=[CH:15][C:16]1[S:20][C:19]([NH2:21])=[N:18][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:6].CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.Cl>C(O)C>[CH2:5]([O:7][C:8](=[O:22])[CH:9]([CH2:15][C:16]1[S:20][C:19]([NH2:21])=[N:18][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6451Bromocresol GreenHCID 5003444Sodium cyanoborohydrideHCID 544471392-(2-Amino-thiazol-5-ylmethylene)-malonic acid diethyl ester

Product 1

HCID 545688642-(2-Amino-thiazol-5-ylmethyl)-malonic acid diethyl esterYield 87.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaCNBH3 (1.88 g; 29.9 mmol) was added to a stirred solution of 2-(2-amino-thiazol-5-ylmethylene)-malonic acid diethyl ester (1.13 g; 4.2 mmol) in ethanol at 0° C. The pH of the solution was monitored by addition of a small amount of Bromocresol Green to the solution. Concentrated HCl was added dropwise until the solution turned yellow. The ice bath was removed, and the reaction mixture was stirred at room temperature for 5 hours. Water was added and the product was extracted with CH2Cl2. The combined organic phases were dried and concentrated to yield 2-(2-amino-thiazol-5-ylmethyl)-malonic acid diethyl ester (1 g, 87.8%).

Workup

  1. customThe ice bath was removed
  2. additionWater was added
  3. extractionthe product was extracted with CH2Cl2
  4. customThe combined organic phases were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-643806574dc7417cbf0983e0af62a5ee
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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