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Phosphorus oxychloride → HCID 178460186, compound

HRID 27275
Notes
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Reaction equation

HRID 27275 reaction equation
[NH2:1][CH:2]1[C:22](=[O:23])[N:4]2[C:5]([C:19]([OH:21])=[O:20])=[C:6]([CH:9]([S:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)[CH2:10][CH2:11][OH:12])[CH2:7][S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.[CH:32]([NH:34][C:35]1[S:36][CH:37]=[C:38]([C:40](=[N:44][O:45][CH2:46][C:47]#[CH:48])[C:41](O)=[O:42])[N:39]=1)=[O:33].P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C.CN(C)C=O>[CH:32]([NH:34][C:35]1[S:36][CH:37]=[C:38]([C:40](=[N:44][O:45][CH2:46][C:47]#[CH:48])[C:41]([NH:1][CH:2]2[C:22](=[O:23])[N:4]3[C:5]([C:19]([OH:21])=[O:20])=[C:6]([CH:9]([S:13][C:14]4[NH:15][N:16]=[N:17][N:18]=4)[CH2:10][CH2:11][OH:12])[CH2:7][S:8][C@H:3]23)=[O:42])[N:39]=1)=[O:33]
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 537194582-(2-Formamidothiazol-4-yl)-2-(propargyloxyimino)acetic acidHCID 178508098HCID 178508098, compound

Product 1

HCID 178460186HCID 178460186, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7-amino-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (2.0 g) and trimethylsilylacetamide (5.9 g) in dry ethyl acetate (40.0 ml) and a solution of 2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetic acid (syn isomer, 1.6 g), dry dimethylformamide (0.5 g) and phosphoryl chloride (1.0 g) in dry ethyl acetate (52.0 ml) were treated in a similar manner to that of Example 1-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetamido]-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (syn isomer, 2.00 g).

Sources & evidence

ORD record
ord-ea89828c3ba04d619ff93379ac9743e3
Source dataset
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04220761

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes