Lithium Hydroxide → HCID 86670247, compound

HRID 872651Notes

Reaction equation

HRID 872651 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9]C)=[O:8])[N:6]=1.Cl[C:12]([O:14][CH3:15])=[O:13].[OH-].[Li+]>N1C=CC=CC=1.C1COCC1.CO>[CH3:15][O:14][C:12]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1)=[O:13]

Participants

6

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 6586Methyl chloroformateHCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylate

Product 1

HCID 86670247HCID 86670247, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 2-aminothiazole-4-carboxylate (1.0 g, 6.32 mmol) was dissolved in dry pyridine and methyl chloroformate (0.733 ml, 9.48 mmol) was added slowly in RT. The reaction mixture was stirred at RT overnight and evaporated to dryness. The evaporation residue was dissolved in dry THF/methanol (9:1) mixture, 1M lithium hydroxide (3.50 ml, 3.50 mmol) was added and the reaction mixture was stirred for 4 h in RT. 1M litium hydroxide (2.33 ml, 2.33 mmol) was added and the mixture was stirred overnight and evaporated to dryness. DCM was added and pH was adjusted to 3. The product was filtered and dried in vacuum. Yield 76%. 1H-NMR (400 MHz; DMSO-d6): δ 3.75 (s, 3H), 7.95 (s, 1H), 12.05 (s, 1H), 12.76 (bs, 1H).

Workup

  1. customevaporated to dryness
  2. additionwas added
  3. stirringthe reaction mixture was stirred for 4 h in RT
  4. stirringthe mixture was stirred overnight
  5. customevaporated to dryness
  6. additionDCM was added
  7. filtrationThe product was filtered
  8. customdried in vacuum

Sources & evidence

ORD record
ord-5a8fc065261b4f73bbd6584ca706d040
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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