Trimethylsilyldiazomethane → HCID 22644909, compound

HRID 2414680Notes

Reaction equation

HRID 2414680 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH:16]([CH2:20][CH2:21][S:22][CH2:23][CH2:24][OH:25])[C:17]([OH:19])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[CH3:26][Si](C=[N+]=[N-])(C)C>CCOCC.CO>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH:16]([CH2:20][CH2:21][S:22][CH2:23][CH2:24][OH:25])[C:17]([O:19][CH3:26])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 22644948HCID 22644948, compound

Product 1

HCID 22644909HCID 22644909, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-4-[(2-hydroxyethyl)sulfanyl]butanoic acid (20.8 g) in ether and methanol was dropwise added trimethylsilyidiazomethane (25 mL. 2.0 M in hexanes). The reaction mixture was concentrated in vacuo and the resulting oil was chromatographed on silica gel eluting with hexane/ethyl acetate to give methyl 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-4-[(2-hydroxyethyl)sulfanyl]butanoate as a light yellow oil (6.68 g). Electrospray Mass Spec 401.9 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting oil was chromatographed on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-186f3689c8e24eea9e26a7eb2f3d3c3a
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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