p-Toluenesulfonic acid monohydrate → (3R,4S)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-4-(1-methyl-1H-tetrazol-4-yl)thio-2-oxoazetidine

HRID 653258Notes

Reaction equation

HRID 653258 reaction equation
[CH3:1][N:2]1[CH2:6][N:5]([S:7][C@@H:8]2[NH:11][C:10](=[O:12])[C@H:9]2[NH:13]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:4]=[N:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:45][CH2:46][C:47]([NH:49][C:50]1[S:51][CH:52]=[C:53]([C:55](=[N:59][O:60][CH3:61])[C:56]([OH:58])=O)[N:54]=1)=[O:48]>CC(C)=O>[Cl:45][CH2:46][C:47]([NH:49][C:50]1[S:51][CH:52]=[C:53]([C:55](=[N:59][O:60][CH3:61])[C:56]([NH:13][C@H:9]2[C@H:8]([S:7][N:5]3[CH2:6][N:2]([CH3:1])[N:3]=[N:4]3)[NH:11][C:10]2=[O:12])=[O:58])[N:54]=1)=[O:48]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 581157C8H8ClN3O4SHCID 54359258(3R,4S)-4-(1-methyl-1H-tetrazol-4-yl)thio-3-tritylamino-2-oxoazetidine

Product 1

HCID 57003025(3R,4S)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-4-(1-methyl-1H-tetrazol-4-yl)thio-2-oxoazetidineYield 55.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the procedure of Reference Example 66B, solution of 1.12 g of (3R,4S)-4-(1-methyl-1H-tetrazol-4-yl)thio-3-tritylamino-2-oxoazetidine in 5 ml of acetone, 0.491 g of p-toluenesulfonic acid monohydrate and 0.788 g of 2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetic acid is treated to give 0.650 g of (3R,4S)-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-4-(1-methyl-1H-tetrazol-4-yl)thio-2-oxoazetidine.

Workup

  1. additionis treated

Sources & evidence

ORD record
ord-af8981b0b7af40b1b1c6ef3fbd29f4b1
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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