Hydrochloric Acid → (+/-) Methyl alpha-(7-Hydroxy-4,5,6,7-tetrahydro-5-thieno[3,2-c]pyridyl)-o-chlorophenylacetate

HRID 2299275Notes

Reaction equation

HRID 2299275 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][CH2:9][N:8]([CH:11]([C:19]([O:21][CH3:22])=[O:20])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[CH:7]=1.Cl>CN(C=O)C>[OH:10][CH:6]1[CH2:7][N:8]([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:19]([O:21][CH3:22])=[O:20])[CH2:9][C:3]2[CH:4]=[CH:5][S:1][C:2]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69853844(+/-) 5-(2-Thienyl)-3-(methoxycarbonyl-o-chlorobenzyl)-1,3-oxazoline

Product 1

HCID 13938216(+/-) Methyl alpha-(7-Hydroxy-4,5,6,7-tetrahydro-5-thieno[3,2-c]pyridyl)-o-chlorophenylacetateYield 86.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-(2-thienyl)-3-(methoxycarbonyl-o-chlorobenzyl)-1,3-oxazoline (22) (5 g, 14.7 mmol) was dissolved in 5 mL of dry DMF and the solution was added dropwise at 0-5° C. over HCl in dry DMF. The reaction was subsequently allowed to warm to room temperature and stirred to complete transformation of the starting material. The solution was partitioned between 1 M sodium bicarbonate solution and toluene. The organic phase was dried on sodium sulfate filtered through a plug of silica gel and evaporated under vacuum to yield 4.3 g of product. 1H-NMR (CDCl3, ppm) 7.45-7.55 (1H, m), 7.35-7.45 (1H, m), 7.2-7.35 (2H, m), 7.2 (1H, d), 6.68 (1H, dd), 5.09 and 5.03 (1H, 2 s), 4.68 (1H, bs), 3.5-4.0 (5H, m), 2.7-3.2 (3H, m).

Workup

  1. customThe solution was partitioned between 1 M sodium bicarbonate solution and toluene
  2. customThe organic phase was dried on sodium sulfate
  3. filtrationfiltered through a plug of silica gel
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-bbfa1ad171c24341bf43070f1cb3af6e
Source dataset
uspto-grants-2002_12
Patent number
US06495691B1

Reaction notes

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