Sodium Bicarbonate → HCID 131715008, compound

HRID 1165979Notes

Reaction equation

HRID 1165979 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:57])[CH:24]([NH:25][C:26](=[O:56])[C:27]([C:40]4[N:41]=[C:42]([NH:45]C(OCC5C=CC=CC=5)=O)[S:43][CH:44]=4)=[CH:28][CH2:29][C:30]([O:32]CC4C=CC=CC=4)=[O:31])[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:58][S:59][C:60]2[N:64]([CH3:65])[N:63]=[N:62][N:61]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])O.[Na+]>C1(OC)C=CC=CC=1>[NH2:45][C:42]1[S:43][CH:44]=[C:40]([C:27](=[CH:28][CH2:29][C:30]([OH:32])=[O:31])[C:26]([NH:25][CH:24]2[C:23](=[O:57])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([CH2:58][S:59][C:60]4[N:64]([CH3:65])[N:63]=[N:62][N:61]=4)[CH2:19][S:20][C@H:21]23)=[O:56])[N:41]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 131715009HCID 131715009, compound

Product 1

HCID 131715008HCID 131715008, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-[2-(2-benzyloxycarbonylamino-4-thiazolyl)-4-benzyloxycarbonyl-2-butenoylamino]-3-(1-methyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid diphenylmethyl ester in anisole (12 parts) is added aluminum chloride (9 equivalents). After stirring for 4 hours at 0° C., the mixture is neutralized with aqueous 5% sodium hydrogen carbonate, filtered to remove solid, and washed with ethyl acetate. Aqueous layer is acidified with hydrochloric acid, washed with ethyl acetate, and passed through a column of HP 20 or SP 207 (synthetic adsorbent produced by Mitsubishi Chemical K. K.). Adsorbed material is eluted with 80% methanol to afford 7-[2-(2-amino-4-thiazolyl)-4-carboxy-2-butenoylamino]-3-(1-methyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid. Yield: 65%.

Workup

  1. filtrationfiltered
  2. customto remove solid
  3. washwashed with ethyl acetate
  4. washwashed with ethyl acetate
  5. custompassed through a column of HP 20 or SP 207 (synthetic adsorbent produced by Mitsubishi Chemical K. K.)
  6. washAdsorbed material is eluted with 80% methanol

Sources & evidence

ORD record
ord-105135c4da994adea64400d59a38c738
Source dataset
uspto-grants-1990_03
Patent number
US04912224

Reaction notes

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