Propylene Oxide → HCID 53956475, compound

HRID 620988Notes

Reaction equation

HRID 620988 reaction equation
[C:1]([S:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O=C(Cl)OC(Cl)(Cl)Cl.[Cl:50][CH2:51][C:52]([NH:54][C:55]1[S:56][CH:57]=[C:58]([C:60](=[N:64][O:65][CH3:66])[C:61]([OH:63])=O)[N:59]=1)=[O:53].C1OC1C>C(N(CC)CC)C.CN(C=O)C.N1C=CC=CC=1>[C:1]([S:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:61](=[O:63])[C:60]([C:58]1[N:59]=[C:55]([NH:54][C:52](=[O:53])[CH2:51][Cl:50])[S:56][CH:57]=1)=[N:64][O:65][CH3:66])(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 6378Propylene OxideHCID 10426DiphosgeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 581157C8H8ClN3O4SHCID 54147732HCID 54147732, compound

Product 1

HCID 53956475HCID 53956475, compoundYield 65.3%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

By employing 0.805 g of (3R,4S)-4-acetylthio-3-tritylamino-2-oxoazetidine, 0.437 g of p-toluenesulfonic acid monohydrate, 0.19 g of pyridine, and, 0.175 g of DMF, 0.144 ml of diphosgene, 0.61 g of 2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetic acid, 0.243 g of triethylamine and 2 ml of propylene oxide, a procedure similar to Reference Example 38B is taken to give 0.548 g of (3R,4S)-4-acetylthio-3-[2-(2-chloroacetoamidothiazole-4-yl)-2-methoxyiminoacetoamido]-2-oxoazetidine.

Sources & evidence

ORD record
ord-72db9bd496504a2888e6b699a6c8ad42
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

Loading…