Phosphorus oxychloride → HCID 178524399, compound

HRID 1902976Notes

Reaction equation

HRID 1902976 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:15][O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:12]([OH:14])=O)[N:10]=1)=[O:4].P(Cl)(Cl)(Cl)=O.[NH2:29][CH:30]1[C:50](=[O:51])[N:32]2[C:33]([C:47]([OH:49])=[O:48])=[C:34]([CH2:37][S:38][C:39]3[N:43](CCO)[N:42]=[N:41][N:40]=3)[CH2:35][S:36][C@H:31]12.C[Si]([CH2:56][C:57](N)=[O:58])(C)C>C(OCC)(=O)C.O1CCCC1.CN(C)C=O>[F:22][C:2]([F:1])([F:23])[C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:15][O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:12]([NH:29][CH:30]2[C:50](=[O:51])[N:32]3[C:33]([C:47]([OH:49])=[O:48])=[C:34]([CH:37]([S:38][C:39]4[NH:43][N:42]=[N:41][N:40]=4)[CH2:56][CH2:57][OH:58])[CH2:35][S:36][C@H:31]23)=[O:14])[N:10]=1)=[O:4]

Participants

8

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 12851091HCID 12851091, compoundHCID 54035027HCID 54035027, compound

Product 1

HCID 178524399HCID 178524399, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-cyclopentyloxyiminoacetic acid (syn isomer, 1.6 g.), dry N,N-dimethylformamide (0.4 g.), phosphoryl chloride (0.8 g.), dry ethyl acetate (1.6 ml.) and tetrahydrofuran (20 ml.), and a solution of 7-amino-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-yl-thiomethyl]-3-cephem-4-carboxylic acid (1.5 g.), trimethylsilylacetamide (3.8 g.) and dry ethyl acetate (30 ml.) were treated in a similar manner to that of Example 1-(1) to give 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-cyclopentyloxyiminoacetamido]-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (syn isomer, 2.63 g.).

Sources & evidence

ORD record
ord-fdd5361cb43d44ffa402355a37fc8c67
Source dataset
uspto-grants-1982_12
Patent number
US04366153

Reaction notes

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