Ammonia → HCID 56634741, compound

HRID 622589Notes

Reaction equation

HRID 622589 reaction equation
C[O:2][C:3]([CH2:5][S:6][C@@H:7]1[NH:10][C:9](=[O:11])[C@H:8]1[NH:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.[NH3:32]>C(O)C>[NH2:32][C:3]([CH2:5][S:6][C@@H:7]1[NH:10][C:9](=[O:11])[C@H:8]1[NH:12][C:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 56636018HCID 56636018, compound

Product 1

HCID 56634741HCID 56634741, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.477 g of (3R,4S)-4-[[(methoxycarbonyl)methyl]thio]-3-tritylamino-2-azetidinone in 5 ml of ethanol is added 1 ml of 25 to 28% aqueous ammonia and the reaction mixture is allowed to stand at room temperature for 2 days. The solvent is then distilled off under reduced pressure and 20 ml of ethyl acetate is added to the residue. The mixture is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography using ethyl acetate-chloroform-methanol (8:8:1) to give 0.173 g of (3R,4S)-4-[[(aminocarbonyl)methyl]thio]-3-tritylamino-2-azetidinone.

Workup

  1. distillationThe solvent is then distilled off under reduced pressure and 20 ml of ethyl acetate
  2. additionis added to the residue
  3. washThe mixture is washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-011c6e2629d748f0a6c6ce67ef3df847
Source dataset
uspto-grants-1988_09
Patent number
US04771045

Reaction notes

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