Diethyl Ether → Methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)thiazole-5-carboxylate

HRID 588501Notes

Reaction equation

HRID 588501 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[S:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][Si](C=[N+]=[N-])(C)C.CCOCC>CO.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[S:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:15]=1)[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 673960092-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 67397774Methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)thiazole-5-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylic acid (1.03 g, 3.8 mmol) in a mixture of MeOH (20 mL) and toluene (20 mL) cooled to 0° C. was added dropwise 2.0M trimethylsilyldiazomethane in ether (12 mL, 24 mmol). The resulting reaction mixture was warmed to room temperature overnight. Excess trimethylsilyldiazomethane was quenched with the addition of acetic acid and the solution concentrated to dryness. The residue was partitioned between EtOAc and saturated aqueous NaHCO3, the organic layer dried over anhydrous Mg2SO4 and concentrated to afford a yellow oil (0.90 g, 83%). LC-MS: (FA) ES+ 287.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas warmed to room temperature overnight
  3. customExcess trimethylsilyldiazomethane was quenched with the addition of acetic acid
  4. concentrationthe solution concentrated to dryness
  5. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  6. dry with materialthe organic layer dried over anhydrous Mg2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e948f13079bb483892368666708274d6
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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