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Acetamide, N-(trimethylsilyl)- → 7-[2-(2-Tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 34494
Notes
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Reaction equation

HRID 34494 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH:32]([F:34])[F:33])[C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.S(Cl)(C)(=O)=O.[NH2:49][CH:50]1[C:67](=[O:68])[N:52]2[C:53]([C:64]([OH:66])=[O:65])=[C:54]([CH2:57][S:58][C:59]3[S:60][CH:61]=[N:62][N:63]=3)[CH2:55][S:56][C@H:51]12.C[Si](C)(C)NC(=O)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1.O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH:32]([F:33])[F:34])[C:27]([NH:49][CH:50]2[C:67](=[O:68])[N:52]3[C:53]([C:64]([OH:66])=[O:65])=[C:54]([CH2:57][S:58][C:59]4[S:60][CH:61]=[N:62][N:63]=4)[CH2:55][S:56][C@H:51]23)=[O:28])[N:25]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 25989Acetamide, N-(trimethylsilyl)-HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 536668022-(2-Tritylamino-4-thiazolyl)-2-difluoromethoxyimino-acetic acid

Product 1

HCID 1317156677-[2-(2-Tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acidYield 83.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-tritylaminothiazol-4-yl)-2difluoromethoxyiminoacetic acid (syn isomer) (0.8 g) and diisopropylethylamine (0.43 g) in N,N-dimethylformamide (20 ml) was added mesyl chloride (0.38 g) at -20° C. and the mixture was stirred at the same temperature for 30 minutes to give an activated acid solution. To a solution of 7-amino-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (0.57 g) and N-trimethylsilylacetamide (1.8 g) in tetrahydrofuran (20 ml) was added the activated acid solution obtained above all at once at -10° C. After being stirred at the same temperature for an hour, the mixture was poured into water and adjusted to pH 2.5 with an aqueous solution of sodium bicarbonate. The precipitates were collected by filtration and washed with water to give 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.1 g).

Workup

  1. customto give an activated acid solution
  2. customobtained above all at once at -10° C
  3. stirringAfter being stirred at the same temperature for an hour
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-ce8d558ac081456ba95239ad58a7474c
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04761410

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes