Acetic Anhydride → Ethyl 5-acetyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate

HRID 2093070Notes

Reaction equation

HRID 2093070 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:13]=2[N:14]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(Cl)(Cl)Cl>[C:22]([N:10]1[CH2:11][CH2:12][C:13]2[N:14]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][C:8]=2[CH2:9]1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 53393419Ethyl 4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine-2-carboxylate

Product 1

HCID 58117030Ethyl 5-acetyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

5-tert-butyl 2-ethyl 6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate obtained in step V of example 1 was deprotected to get the 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester. To a solution of 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester (1 eq) and triethyl amine (1 eq) in chloroform, acetic anhydride was added and the reaction mixture was stirred for 1 h at room temperature. Reaction mixture was then diluted with chloroform and washed with water. Organic layer was then separated, dried and concentrated under reduced pressure to afford the desired ethyl 5-acetyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate.

Workup

  1. customReaction mixture
  2. washwashed with water
  3. customOrganic layer was then separated
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6247cc38c67d43f383d7c09b22f07b0a
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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