Sodium Iodide → Acetoxymethyl 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxyethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate

HRID 904919Notes

Reaction equation

HRID 904919 reaction equation
[C:1]([O:4][CH2:5]Cl)(=[O:3])[CH3:2].[I-].[Na+].C(OCI)(=O)C.[N:15]([CH2:18][C:19]1[CH2:20][S:21][C@@H:22]2[CH:29]([NH:30][C:31](=[O:65])[C:32]([C:40]3[N:41]=[C:42]([NH:45][C:46]([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[S:43][CH:44]=3)=[N:33][O:34][C:35]([CH3:39])([O:37][CH3:38])[CH3:36])[C:28](=[O:66])[N:23]2[C:24]=1[C:25]([OH:27])=[O:26])=[N+:16]=[N-:17]>CC(C)=O>[N:15]([CH2:18][C:19]1[CH2:20][S:21][C@@H:22]2[CH:29]([NH:30][C:31](=[O:65])[C:32]([C:40]3[N:41]=[C:42]([NH:45][C:46]([C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=4)([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)[C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[S:43][CH:44]=3)=[N:33][O:34][C:35]([CH3:36])([O:37][CH3:38])[CH3:39])[C:28](=[O:66])[N:23]2[C:24]=1[C:25]([O:27][CH2:5][O:4][C:1](=[O:3])[CH3:2])=[O:26])=[N+:16]=[N-:17]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 69366Chloromethyl acetateHCID 11820084Iodomethyl acetateHCID 1317132523-Azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxyethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid

Product 1

HCID 131713259Acetoxymethyl 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxyethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 141 mg of chloromethyl acetate, 225 mg of sodium iodide and 4 ml of acetone was refluxed for 40 minutes and was cooled to obtain a suspension of iodomethyl acetate. Using the procedure of Step B of Example 6, 739 mg of 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxy-ethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid and the said suspension were reacted to obtain 698 mg of the syn isomer of acetoxymethyl 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxyethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate.

Workup

  1. temperaturewas refluxed for 40 minutes
  2. temperaturewas cooled
  3. customto obtain
  4. customthe said suspension were reacted

Sources & evidence

ORD record
ord-ba53b00d6ce94feea7d70234a0424415
Source dataset
uspto-grants-1983_12
Patent number
US04420478

Reaction notes

Loading…