Sodium Carbonate → HCID 178451386, compound

HRID 1902973Notes

Reaction equation

HRID 1902973 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]([OH:12])=O)[N:8]=1)=[O:2].P(Cl)(Cl)(Cl)=O.[NH2:28][CH:29]1[C:57](=[O:58])[N:31]2[C:32]([C:54]([OH:56])=[O:55])=[C:33]([CH:36]([S:48][C:49]3[NH:53][N:52]=[N:51][N:50]=3)[CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:34][S:35][C@H:30]12.C(=O)([O-])[O-].[Na+].[Na+]>O.CC(C)=O.O1CCCC1.CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]([NH:28][CH:29]2[C:57](=[O:58])[N:31]3[C:32]([C:54]([OH:56])=[O:55])=[C:33]([CH:36]([S:48][C:49]4[NH:50][N:51]=[N:52][N:53]=4)[CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:42])[CH2:34][S:35][C@H:30]23)=[O:12])[N:8]=1)=[O:2]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 543909512-t-Butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acidHCID 178453487HCID 178453487, compound

Product 1

HCID 178451386HCID 178451386, compoundYield 99.8%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetic acid (syn isomer, 16.5 g.), N,N-dimethylformamide (4.4 g.), phosphoryl chloride (9.2 g.), 7-amino-3-[1-(3-tert-butoxycarbonylaminopropyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (23.6 g.), sodium carbonate (5.3 g.), tetrahydrofuran (100 ml.), acetone (150 ml.) and water (150 ml.) were treated in a similar manner to that of Example 11-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[1-(3-tert-butoxycarbonylaminopropyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (syn isomer, 39.1 g.).

Sources & evidence

ORD record
ord-c021d643d77f4723884643ff8b0d5b1e
Source dataset
uspto-grants-1982_12
Patent number
US04366153

Reaction notes

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