Tetrahydrofuran → HCID 53714300, compound

HRID 1018149Notes

Reaction equation

HRID 1018149 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:12][CH2:11][CH2:10][CH2:9]1)=O.C1COCC1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[S:46]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 54133083HCID 54133083, compound

Product 1

HCID 53714300HCID 53714300, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
62.5 °C

Procedure

To a solution of N-[[1-[4-(methylsulfonyl)butyl]cyclopentyl]carbonyl]-4-nitro-L-phenylalanine methyl ester (33 mmol, 15 g) in toluene (100 mL, stored over 4 Å molecular sieves) and freshly distilled THF (50 mL) was added Lawesson's reagent (33 mmol, 13.35 g, 1.0 equiv.) at room temperature. The solution was heated to 60-65° C. and was stirred for 48 h at which time TLC analysis of the mixture indicated the absence of starting material. The reaction mixture was cooled to room temperature and was poured into saturated sodium bicarbonate solution (200 mL) and extracted with ethyl acetate (3×150 mL). An oil formed in the aqueous layer, which was separated, diluted with water and extracted with ethyl acetate (2×50 mL). The combined ethyl acetate extracts were washed with saturated sodium bicarbonate solution (200 mL), with brine (300 mL), dried (MgSO4), filtered and the solution was concentrated in vacuo. The residual light brown syrup was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1) to obtain 6.87 g (44%) of N-[[1-[4-(methylsulfonyl)butyl]cyclopentyl]thioxo-methyl]-4-nitro-L-phenylalanine methyl ester as a fluffy yellow solid. HRMS: Obs. mass, 493.1438. Calcd. mass, 493.1443 (M+Na).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. customAn oil formed in the aqueous layer, which
  4. customwas separated
  5. additiondiluted with water
  6. extractionextracted with ethyl acetate (2×50 mL)
  7. washThe combined ethyl acetate extracts were washed with saturated sodium bicarbonate solution (200 mL), with brine (300 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationthe solution was concentrated in vacuo
  11. customThe residual light brown syrup was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-e65e7895ba4841f7ab5162161e7b8dbc
Source dataset
uspto-grants-2002_11
Patent number
US06479666B2

Reaction notes

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