Water → HCID 54141665, compound

HRID 2395367Notes

Reaction equation

HRID 2395367 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([NH:17][C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([I:25])[CH:20]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1.O>COCCOC>[Si:1]([O:8][CH2:9][C@H:10]([NH:17][C:18](=[S:36])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([I:25])[CH:20]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 54520784HCID 54520784, compound

Product 1

HCID 54141665HCID 54141665, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of N-(1-tert-butyldimethylsilyloxy-2(R)-phenylethan-2-yl)-3-iodobenzamide (13.1 g, 27.2 mmol) in 1,2-dimethoxyethane (80 ml) was added Lawesson's reagent (8.2 g, 20 mmol). The reaction mixture was stirred at ambient temperature for 1 h and then at 60° C. for 2 hours, cooled and poured into water (100 ml). The mixture was extracted with CH2 Cl2 (2×50 ml), washed with brine (100 ml), dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (=1:7) to afford N-(1-tert-butyldimethylsilyloxy-2(R)-phenyl-ethan-2-yl)-3-iodobenzthiamide (4.99 g, 50%) as a yellow liquid.

Workup

  1. waitat 60° C. for 2 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted with CH2 Cl2 (2×50 ml)
  4. washwashed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (=1:7)

Sources & evidence

ORD record
ord-5ee82212564b4562b03098b23b4603c8
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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