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Dicyclohexylcarbodiimide → Tert.-butyl 7-[2-(2-tritylamino-4thiazolyl)-2-tetrahydropyranyloxyimino-acetamido]-3-acetoxymethyl-ceph-3-eme-4-carboxylate

HRID 1905582
Notes
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Reaction equation

HRID 1905582 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[C:27]([OH:29])=O)[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.[NH2:38][CH:39]1[C:58](=[O:59])[N:41]2[C:42]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[C:43]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[CH2:44][S:45][C@H:40]12.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[C:27]([NH:38][CH:39]2[C:58](=[O:59])[N:41]3[C:42]([C:51]([O:53][C:54]([CH3:56])([CH3:55])[CH3:57])=[O:52])=[C:43]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[CH2:44][S:45][C@H:40]23)=[O:29])[N:25]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 15573429t-Butyl 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylateHCID 538028372-(2-Tritylamino-4-thiazolyl)-2-tetrahydropyranyloxyimino-acetic acid

Product 1

HCID 131711731Tert.-butyl 7-[2-(2-tritylamino-4thiazolyl)-2-tetrahydropyranyloxyimino-acetamido]-3-acetoxymethyl-ceph-3-eme-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.362 g of the product of Step C, 0.244 g of tert.-butyl 7-amino-3-acetoxymethyl-ceph-3-eme-4-carboxylate, 0.280 g of dicyclohexylcarbodiimide and 4 ml of dry chloroform was stirred for 2 hours at room temperature and the mixture was vacuum filtered to remove dicyclohexylurea which was rinsed with chloroform. The filtrate was evaporated to dryness under reduced pressure and the residue was dissolved in 1 ml of ether. The solution was chromatographed over silica gel and was eluted with ether. The fractions with an Rf=0.38 were combined and evaporated to dryness under reduced pressure. The residue was taken up in isopropyl ether and effloresced. The mixture was vacuum filtered and the recovered product was rinsed with isopropyl ether to obtain 0.184 g of the syn isomer of tert.-butyl 7-[2-(2-tritylamino-4-thiazolyl)-2-tetrahydropyranyloxyimino-acetamido]-3-acetoxymethyl-ceph-3-eme-4-carboxylate.

Workup

  1. filtrationfiltered
  2. customto remove dicyclohexylurea which
  3. washwas rinsed with chloroform
  4. customThe filtrate was evaporated to dryness under reduced pressure
  5. dissolutionthe residue was dissolved in 1 ml of ether
  6. customThe solution was chromatographed over silica gel
  7. washwas eluted with ether
  8. customevaporated to dryness under reduced pressure
  9. filtrationfiltered
  10. washthe recovered product was rinsed with isopropyl ether

Sources & evidence

ORD record
ord-651bfae74e514281bc20122ea30e70b3
Source dataset
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04843164

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes