Calcium Carbonate → 2-Phenoxycarbonylamino-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester

HRID 239102Notes

Reaction equation

HRID 239102 reaction equation
C(=O)([O-])[O-].[Ca+2].Cl[C:7]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8].[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26]2[N:29]=[C:30]([NH2:32])[S:31][C:25]=2[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26]2[N:29]=[C:30]([NH:32][C:7]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:8])[S:31][C:25]=2[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 15891Phenyl chloroformateHCID 11357283tert-butyl 2-amino-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate

Product 1

HCID 866860322-Phenoxycarbonylamino-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl esterYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

39 g calcium carbonate and 36.8 g phenyl chloroformate in 250 mL THF was added to a stirred solution of 50 g 2-amino-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester in 1 L THF. The reaction mixture was allowed to stir for 15 h at RT. The reaction mixture was filtered through silica gel and the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate and the organic layer was dried over magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was washed with 20% ethyl acetate in hexane to give 60 g of the desired product.

Workup

  1. filtrationThe reaction mixture was filtered through silica gel
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. washThe residue was washed with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1a701deefd8e4b64a92103bf431b87ed
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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