Trimethylsilyldiazomethane → HCID 54219368, compound

HRID 1760796Notes

Reaction equation

HRID 1760796 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([NH:13][C@H:14]([CH2:18][O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:15]([OH:17])=[O:16])(=[O:12])=[O:11])=[C:5]([CH3:24])[C:4]=1[CH3:25].[CH3:26][Si](C=[N+]=[N-])(C)C>CO.C(Cl)Cl>[CH3:26][O:16][C:15](=[O:17])[C@H:14]([NH:13][S:10]([C:6]1[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:25])[C:5]=1[CH3:24])(=[O:12])=[O:11])[CH2:18][O:19][C:20]([CH3:21])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 18337546HCID 18337546, compound

Product 1

HCID 54219368HCID 54219368, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3-tert-butoxypropionic acid (2.79 g, 7.5 mmol) in 70% methanol/methylene chloride (50 mL) at 0° C. was added 1M trimethylsilyldiazomethane in hexanes (22.5 mL, 23 mmol). After 45 min., the reaction mixture was concentrated and chromatographed using preparative chromatography (9% ethyl acetate-hexanes) to afford 2(R)-(4-methoxy-2,3,6-trimethyl-benzenesulfonylamino)-3-tert-butoxypropionic acid methyl ester (2.4 g).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customchromatographed

Sources & evidence

ORD record
ord-84b72e47b93841708f9f2851e25ad2e1
Source dataset
uspto-grants-2005_01
Patent number
US06844366B2

Reaction notes

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