Methanol → (2S,3R)-methyl 3-azido-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

HRID 1783438Notes

Reaction equation

HRID 1783438 reaction equation
[N:1]([C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C@@H:5]1[C:16]([OH:18])=[O:17])=[N+:2]=[N-:3].CO.[CH2:21]1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:1]([C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:14])([CH3:15])[CH3:13])([CH3:11])[CH3:10])[C@@H:5]1[C:16]([O:18][CH3:21])=[O:17])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 13712291(2S,3R)-1-t-butyldimethylsilyl-3-azido-4-oxo-2-azetidinecarboxylic acid

Product 1

HCID 57589884(2S,3R)-methyl 3-azido-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 131 (1.58 g) in CH2Cl2 (25 mL) was added methanol (0.26 mL, 6.43 mmol). DCC (1.45 g, 7.02 mmol) and catalytic DMAP. The solution was stirred at room temperature overnight. The solution was then filtered through Celite and concentrated in vacuo. The crude product was purified by silica gel column chromatography, eluting with 20% EtOAc in hexanes, to yield pure 132.

Workup

  1. filtrationThe solution was then filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by silica gel column chromatography
  4. washeluting with 20% EtOAc in hexanes
  5. customto yield pure 132

Sources & evidence

ORD record
ord-635b4696e07342a98a906857c2e01f9a
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

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