HCID 141545489, compound → HCID 178502829, compound

HRID 483022Notes

Reaction equation

HRID 483022 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:57]/[O:58][CH3:59])/[C:27]([NH:29][C@@H:30]2[C:55](=[O:56])[N:32]3[C:33]([C:52]([OH:54])=[O:53])=[C:34]([CH2:37][S:38][C:39]4[N:43]([N:44]=[CH:45][C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[N:42]=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[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(O)=O>[CH:52]([OH:54])=[O:53].[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:57]/[O:58][CH3:59])/[C:27]([NH:29][C@@H:30]2[C:55](=[O:56])[N:32]3[C:33]([C:52]([OH:54])=[O:53])=[C:34]([CH2:37][S:38][C:39]4[N:43]([N:44]=[CH:45][C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)[N:42]=[N:41][N:40]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 141545489HCID 141545489, compound

Product 1

HCID 178502829HCID 178502829, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2.92 g of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1-benzylideneamino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid were dissolved in 15 ml of 80% formic acid, and the solution was stirred at room temperature for 2 hours. The precipitates were collected by filtration, washed with a mixture of 3 ml of isopropanol and 3 ml of ether, and then dried. 1.61 g of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1-benzylideneamino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid formate thus obtained were dissolved in 20 ml of tetrahydrofuran. The resultant precipitates were collected by filtration, washed with isopropanol and ether, and then dried. The pale yellow powder thus obtained was dissolved in 15 ml of water. The aqueous solution was passed through the column packed with 50 ml of a styrene-divinylbenzene copolymer (Trade name "Diaion HP-20"). After the column was washed with water, said column was eluted with 20% aqueous ethanol. Then, the eluates obtained were freeze-dried. 1.01 g of 7β-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1-benzylideneamino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid sodium salt were thereby obtained as pale yellow powder.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with a mixture of 3 ml of isopropanol and 3 ml of ether
  3. customdried

Sources & evidence

ORD record
ord-89c2d52c4bd94f40a71a36b2616c6254
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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