Diisopropylethylamine → 3-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester

HRID 1881044Notes

Reaction equation

HRID 1881044 reaction equation
[S:1]([C:4]1[S:8][C:7]([NH2:9])=[N:6][CH:5]=1)[C:2]#N.[BH4-].[Na+].Br[CH2:13][C:14]([CH3:19])(C)[C:15]([OH:17])=[O:16].[CH:20](N(C(C)C)CC)(C)[CH3:21]>CO.O>[CH2:20]([O:17][C:15](=[O:16])[C:14]([CH3:19])([CH3:13])[CH2:2][S:1][C:4]1[S:8][C:7]([NH2:9])=[N:6][CH:5]=1)[CH3:21]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2719323-Bromo-2,2-dimethylpropanoic acidHCID 3109677[(2-Amino-1,3-thiazol-5-yl)sulfanyl]formonitrileHCID 4311764Sodium borohydride

Product 1

HCID 574814293-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

5-thiocyanato-thiazol-2-ylamine (15.7 g) was dissolved in degassed methanol and sodium borohydride (4.5 g) in MeOH was added in one portion. The reaction was stirred for 30 min and 3-bromo-2,2-dimethyl-propionic acid (27 g) and diisopropylethylamine(17 mL) was added and the reaction stirred overnight at room temperature. The reaction was diluted with water, partially concentrated in vacuo and 5% citric acid was added until pH 4. The brown precipitate was filtered, washed with water and acetonitrile, and dried over night at room temperature. The residue was stirred with ethanol, filtered, washed with ethanol and dried in a vacuum oven at 40° C. to give 3-(2-amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester.

Workup

  1. stirringthe reaction stirred overnight at room temperature
  2. concentrationpartially concentrated in vacuo and 5% citric acid
  3. additionwas added until pH 4
  4. filtrationThe brown precipitate was filtered
  5. washwashed with water and acetonitrile
  6. customdried over night at room temperature
  7. stirringThe residue was stirred with ethanol
  8. filtrationfiltered
  9. washwashed with ethanol
  10. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-c723aa2936074c58980d3493d9910955
Source dataset
uspto-grants-2012_11
Patent number
US08318778B2

Reaction notes

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