Phloroglucinol → HCID 131709921, compound

HRID 1580488Notes

Reaction equation

HRID 1580488 reaction equation
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].C(O[CH2:14][C:15]1[CH:20]([C:21]([OH:23])=[O:22])[N:19]2[C:24](=[O:36])[CH:25]([NH:26][C:27](=[O:35])[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:18]2[S:17][CH:16]=1)(=O)C>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[C:29]1([CH2:28][C:27]([NH:26][CH:25]2[C:24](=[O:36])[N:19]3[CH:20]([C:21]([OH:23])=[O:22])[C:15]([CH2:14][C:9]4[C:1]([OH:2])=[CH:3][C:4]([OH:5])=[CH:6][C:7]=4[OH:8])=[CH:16][S:17][C@H:18]23)=[O:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 359PhloroglucinolHCID 131709916HCID 131709916, compound

Product 1

HCID 131709921HCID 131709921, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.063 g of phloroglucinol in 0.3 ml of trifluoroacetic acid is mixed with 0.04 g of 3-acetoxymethyl-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid, and the solution is left to stand for 30 minutes at room temperature and diluted with an equal quantity of toluene. The mixture is evaporated to dryness under reduced pressure and the residue is worked up in accordance with the process described in example 6. 7-(N-Phenylacetyl-amino)-3-(2,4,6-trihydroxy-benzyl)-ceph-2-em-4ξ-carboxylic acid is thus obtained, showing the following Rf values in a thin layer chromatogram (silica gel): 0.73 (system n-butanol/acetic acid/water, 67:10:23) and 0.55 (system n-butanol/ethanol/water, 40:10:50).

Workup

  1. waitthe solution is left
  2. customThe mixture is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ae8598b3a3d54fa8b2c096be53de0e6c
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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