Methyl 5-bromovalerate → HCID 18963778, compound

HRID 2226864Notes

Reaction equation

HRID 2226864 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[SH:10][C:11]1[C:12]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:13]=2[S:14][C:15]=1[C:16]([NH2:18])=[O:17].C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[NH2:18][C:16]([C:15]1[S:14][C:13]2[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:12]=2[C:11]=1[S:10][CH:4]([CH2:3][CH3:2])[CH2:5][C:6]([O:8][CH3:9])=[O:7])=[O:17]

Participants

6

Reactant 3

HCID 79557Methyl 5-bromovalerate2×HCID 516892Sodium BicarbonateHCID 10847601HCID 10847601, compound

Product 1

HCID 18963778HCID 18963778, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 5-bromovalerate (144 μL, 1.00 mmol) is added to a room temperature solution of 3-mercapto-5-methoxybenzo[b]thiophene-2-carboxamide (200 mg, 0.84 mmol) in 8 mL of THF followed by NaHCO3 (351 mg, 4.18 mmol) and the reaction mixture is stirred at room temperature overnight. Additional methyl 5-bromovalerate (100 μL) is added and the reaction mixture is stirred at room temperature for 3 days. The reaction mixture is diluted with ethyl acetate and washed with 1N HCl, water, saturated NaHCO3, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane gives methyl 3-[[2-(aminocarbonyl)-5-methoxybenzo[b]thien-3-yl]thio]pentanoate in 30% yield; mp=134.5°-135.5° C.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 3 days
  2. washwashed with 1N HCl, water, saturated NaHCO3, and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationFiltration
  5. concentrationfollowed by concentration in vacuo and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-15c22a771b93422092a57386fb94e17a
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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