Trimethylsilyldiazomethane → HCID 53241888, compound

HRID 422161Notes

Reaction equation

HRID 422161 reaction equation
[OH:1][C:2]1[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]2[C:3]=1[C@@:4]1([CH3:26])[C@H:13]([CH2:14][S:15]2(=[O:22])=[O:21])[C@:12]2([CH3:23])[C@H:7]([C:8]([CH3:25])([CH3:24])[CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5]1.[CH3:27][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[OH:1][C:2]1[CH:19]=[C:18]([O:20][CH3:27])[CH:17]=[C:16]2[C:3]=1[C@@:4]1([CH3:26])[C@H:13]([CH2:14][S:15]2(=[O:22])=[O:21])[C@:12]2([CH3:23])[C@H:7]([C:8]([CH3:25])([CH3:24])[CH2:9][CH2:10][CH2:11]2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 53241887HCID 53241887, compound

Product 1

HCID 53241888HCID 53241888, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,10R,11S,16S)-3,5-dihydroxy-1,11,15,15-tetramethyl-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (28) (8.0 g, 21 mmol) in CH2Cl2 (192 mL) and methanol (64 mL), (trimethylsilyl)diazomethane (2 M in diethyl ether, 16.9 mL, 33.8 mmol) was added in 2 mL increments every hour at room temperature under N2. The mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated to dryness and the residue was purified by flash chromatography on silica gel (Hexanes/EtOAc, 2:1) to yield (1R,10R,11S,16S)-3-hydroxy-5-methoxy-1,11,15,15-tetramethyl-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (30) (4.9 g, 58%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was purified by flash chromatography on silica gel (Hexanes/EtOAc, 2:1)

Sources & evidence

ORD record
ord-25a43e8694da4dc9a2a05fe64f449e41
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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