Ammonia → (trans)-3-t-Butoxycarbonylamino-4-ethyl-2-azetidinone

HRID 371221Notes

Reaction equation

HRID 371221 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH2:13][CH3:14])[N:11](OC)[C:10]1=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].N.[Na].[Cl-].[NH4+]>>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH2:13][CH3:14])[NH:11][C:10]1=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 70415672(trans)-3-t-Butoxycarbonylamino-4-ethyl-1-methoxy-2-azetidinone

Product 1

HCID 70415750(trans)-3-t-Butoxycarbonylamino-4-ethyl-2-azetidinoneYield 102.6%

Procedure

(trans)-3-t-Butoxycarbonylamino-4-ethyl-1-methoxy-2-azetidinone (3 g) is added to 170 ml of liquid ammonia at -78° C. under nitrogen and 1.68 g of sodium is added in 5 portions with stirring over a 5 minute period. Stirring is continued for 30 minutes. Ammonium chloride is then added slowly until the blue color of the reaction mixture disappears. After removal of the ammonia under nitrogen the solid is extracted with two 100 ml portions of ethyl acetate. Removal of the solvent followed by drying in vacuo yields 2.7 g of the title compound.

Workup

  1. stirringStirring
  2. waitis continued for 30 minutes
  3. customAfter removal of the ammonia under nitrogen the solid
  4. extractionis extracted with two 100 ml portions of ethyl acetate
  5. customRemoval of the solvent
  6. customby drying in vacuo

Sources & evidence

ORD record
ord-4d1e597e2e3147808113bcc8a1b02158
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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