Hexane → 7-[2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyimino-acetylamino]-3-formyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

HRID 1633811Notes

Reaction equation

HRID 1633811 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH2:25][OH:26])[CH:20]([NH:27][C:28](=[O:57])[C:29]([C:51]1[N:55]=[C:54]([NH2:56])[S:53][N:52]=1)=[N:30][O:31][C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:19]2=[O:58])=[O:16])([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(OCC)(=O)C.CCCCCC>O1CCCC1.ClCCl.O=[Mn]=O.[O-2].[O-2].[Mn+4]>[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH:25]=[O:26])[CH:20]([NH:27][C:28](=[O:57])[C:29]([C:51]1[N:55]=[C:54]([NH2:56])[S:53][N:52]=1)=[N:30][O:31][C:32]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:19]2=[O:58])=[O:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 764716187-[2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyimino-acetylamino]-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Product 1

HCID 731640087-[2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyimino-acetylamino]-3-formyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl esterYield 52.1%

Reagents, catalysts & solvents 4

HCID 14801Manganese dioxideCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.2 (via MnO2): To a solution of 10.00 g (12.36 mMol) 7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyimino-acetylamino]-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester in 100 ml tetrahydofurane and 100 ml dichloromethane is added in 13 portions in 15 min intervals 65 g manganese dioxide (0.75 Mol) with stirring. To the resulting suspension is added 10.0 g active coal and 500 ml ethyl acetate. The mixture is concentrated to a volume of 200 ml. To resulting suspension is added 100 ml n hexane and the mixture is purified by chromatography over 500 g silica gel using 1:2 mixture of n hexane: ethyl acetate as eluent. The product fraction are collected and evaporated to dryness under aspirator vacuum. The resulting foam is triturated with 30 ml t-butylmethyl ether to give 5.2 g of the title compound as a yellowish powder with identical analytical characteristics as in example 2.1.

Workup

  1. concentrationThe mixture is concentrated to a volume of 200 ml
  2. customTo resulting suspension
  3. customthe mixture is purified by chromatography over 500 g silica gel using 1:2 mixture of n hexane
  4. customThe product fraction are collected
  5. customevaporated to dryness under aspirator vacuum
  6. customThe resulting foam is triturated with 30 ml t-butylmethyl ether

Sources & evidence

ORD record
ord-bacea6ed73ff401fa5c8a58e700948c1
Source dataset
uspto-grants-2003_01
Patent number
US06504025B2

Reaction notes

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