Ammonia → HCID 13478178, compound

HRID 371224Notes

Reaction equation

HRID 371224 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:11](OC)[C:10]1=[O:21])=[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]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[NH:11][C:10]1=[O:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545Sodium2×HCID 13478175HCID 13478175, compound

Product 1

HCID 13478178HCID 13478178, compound

Procedure

(trans)-3-(t-Butoxycarbonylamino)-4-cyclohexyl-1-methoxy-2-azetidinone (1 g) is added to 50 ml of liquid ammonia with stirring. Sodium (0.154 g) is added in 5 to 6 portions within 5 minutes. After this time an additional amount of 0.025 g sodium is added and stirring is continued for 5 minutes. Ammonium chloride (0.89 g) is added and the ammonia is removed. The residue is extracted with warm ethyl acetate. The organic extract is evaporated to dryness and the remaining crystals of the title compound are filtered with petrol ether, yielding 0.5 g, melting point 130°-132° C.

Workup

  1. stirringstirring
  2. customthe ammonia is removed
  3. extractionThe residue is extracted with warm ethyl acetate
  4. extractionThe organic extract
  5. customis evaporated to dryness
  6. filtrationthe remaining crystals of the title compound are filtered with petrol ether
  7. customyielding 0.5 g, melting point 130°-132° C.

Sources & evidence

ORD record
ord-80fa64e0edd64bea996e2fbb2ebcc05f
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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