Acetic Acid → (2S,3R)-3-Allyl-4-oxo-azetidine-2-carboxylic acid 4-methoxy-benzyl ester

HRID 1783426Notes

Reaction equation

HRID 1783426 reaction equation
[F-].[NH4+].[CH3:3][O:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][O:10][C:11]([C@@H:13]2[C@@H:16]([CH2:17][CH:18]=[CH2:19])[C:15](=[O:20])[N:14]2[Si](C(C)(C)C)(C)C)=[O:12])=[CH:7][CH:6]=1.C(O)(=O)C>CO>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11]([C@@H:13]2[C@@H:16]([CH2:17][CH:18]=[CH2:19])[C:15](=[O:20])[NH:14]2)=[O:12])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 25516Ammonium fluorideHCID 57589741(2S,3R)-3-Allyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid 4-methoxy-benzyl ester

Product 1

HCID 57589773(2S,3R)-3-Allyl-4-oxo-azetidine-2-carboxylic acid 4-methoxy-benzyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 6.2 mL of 0.5 M ammonium fluoride in methanol (3.1 mmol) was added to a mixture of compound 58 (1.0 g, 2.57 mmol), acetic acid (530 uL, 9.0 mmol) and methanol (25 mL). The mixture was stirred at room temperature for 2 h. The solvent was removed and the residue was taken up in toluene (2˜3 mL) to assist removal of AcOH. After solvent was removed, the residue was taken up in DCM. The resulting white solids were filtered off. Concentration of the filtrate gave 0.70 g of the crude 59 with purity: 91.1%, 1HNMR (300 MHz, CDCl3): 2.60 (m, 2H), 3.38 (m, 1H), 3.87 (s, 3H), 3.98 (d, 1H), 5.22 (m, 4H), 5.83 (m, 1H), 6.15 (b, s, 1H), 6.90 (d, 2H), 7.35 (d, 2H). Anal. C15H17NO4, Mol. Wt.: 275.3. Found: ESI-MS: 275.8 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customremoval of AcOH
  3. customAfter solvent was removed
  4. filtrationThe resulting white solids were filtered off
  5. customConcentration of the filtrate gave 0.70 g of the crude 59 with purity: 91.1%, 1HNMR (300 MHz, CDCl3): 2.60 (m, 2H), 3.38 (m, 1H), 3.87 (s, 3H), 3.98 (d, 1H), 5.22 (m, 4H), 5.83 (m, 1H), 6.15 (b, s, 1H), 6.90 (d, 2H), 7.35 (d, 2H)

Sources & evidence

ORD record
ord-c4be8430d39044e3ab8d1d14f53eb25f
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

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