HCID 15058021, compound → HCID 15058025, compound

HRID 1709364Notes

Reaction equation

HRID 1709364 reaction equation
C(O[CH2:5][C:6]#[C:7][C@@H:8]1[NH:11][C:10](=[O:12])[C@H:9]1[NH:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)C>[Pt]=O>[CH2:7]([C@@H:8]1[NH:11][C:10](=[O:12])[C@H:9]1[NH:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][CH3:5]

Participants

3

Reactant 1

HCID 15058021HCID 15058021, compound

Product 1

HCID 15058025HCID 15058025, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

420 mg (1 mmol) of 3-[(3S,4S)-2-oxo-3-tritylamino-4-azetidinyl]-2-propynyl acetate are hydrogenated in the same manner with platinum oxide and the product is chromatographed over 70 g of silica gel with t-butyl methyl ether/n-hexane (1:1). After 125 ml, there are obtained 300 mg of (3S,4S)-4-propyl-3-tritylamino-2-azetidinone and, after 275 ml, there are obtained 87 mg of 3-[(3S,4S)-2-oxo-3-tritylamino-4-azetidinyl]-propyl acetate.

Workup

  1. customthe product is chromatographed over 70 g of silica gel with t-butyl methyl ether/n-hexane (1:1)

Sources & evidence

ORD record
ord-aaea6b703b42424a860ce379e9d9b1d4
Source dataset
uspto-grants-1990_08
Patent number
US04948898

Reaction notes

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