Hydrochloric Acid → HCID 66747630, compound

HRID 2402076Notes

Reaction equation

HRID 2402076 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[N:8]=[C:9]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[S:10][C:11]=2[C:12]([O:14]CC)=[O:13])=[CH:4][CH:3]=1.O.[Li+].[OH-].Cl>C1COCC1>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[N:8]=[C:9]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[S:10][C:11]=2[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 66748298HCID 66748298, compound

Product 1

HCID 66747630HCID 66747630, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(4-chlorobenzyl)-2-morpholinothiazole-5-carboxylate (3.44 g, 9.38 mmol) in THF (53 mL) was added water (26 mL) and 1 N LiOH (28.2 mL, 28.2 mmol) and the resulting mixture was heated to 40 degrees overnight. The reaction was cooled, acidified with 1 N HCl, and extracted with ethyl acetate (3×50 mL). The combined ethyl acetate layers were dried over MgSO4, filtered, and concentrated to give the crude product, which was purified by silica gel chromatography (methanol/DCM=0/100→20/80). Recrystallization from ethyl acetate/hexanes gave 1.3 g of the title compound as a white solid. (41% yield). LC/MS (FA) ES+ 339. 1H NMR (400 MHz, DMSO-d6) δ: 12.74 (s, 1H), 7.33-7.30 (m, 2H), 7.26-7.23 (m, 2H), 4.21 (s, 2H), 3.67-3.64 (m, 4H), 3.42-3.40 (m, 4H).

Workup

  1. temperaturethe resulting mixture was heated to 40 degrees overnight
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined ethyl acetate layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by silica gel chromatography (methanol/DCM=0/100→20/80)
  9. customRecrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9837359cf1ba400bae53dc852a368be7
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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