Hydrochloric Acid → HCID 178433976, compound

HRID 1858529Notes

Reaction equation

HRID 1858529 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7]C=O)=[N:4][C:3]=1[CH2:10][C:11]([NH:13][C@@H:14]1[C:30](=[O:31])[N:16]2[C:17]([C:27]([OH:29])=[S:28])=[C:18]([C:21]3[S:22][C:23]([CH3:26])=[N:24][N:25]=3)[CH2:19][S:20][C@H:15]12)=[O:12].CO.Cl.[OH-].[Na+]>C(OCC)(=O)C.O1CCCC1>[NH2:7][C:5]1[S:6][C:2]([Cl:1])=[C:3]([CH2:10][C:11]([NH:13][C@@H:14]2[C:30](=[O:31])[N:16]3[C:17]([C:27]([OH:29])=[S:28])=[C:18]([C:21]4[S:22][C:23]([CH3:26])=[N:24][N:25]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 14798Sodium HydroxideHCID 178433975HCID 178433975, compound

Product 1

HCID 178433976HCID 178433976, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent3×

Conditions

Temperature
35 °C

Procedure

To a suspension of 7β-[2-(5-chloro-2-formylaminothiazol-4-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylic acid (380 mg), methanol (4 ml) and tetrahydrofuran (4 ml) was conc-hydrochloric acid (153 μl). The mixture was stirred for 5 hours at 35° C. The reaction mixture was added to a mixture of ethyl acetate (20 ml) and ice-water (50 ml). To the aqueous solution was added ethyl acetate (20 ml). The mixture was adjusted to pH 7 with 1N-sodium hydroxide solution. To the separated aqueous solution was added ethyl acetate (20 ml). The mixture was adjusted to pH 2 with 1N-hydrochloric acid. The precipitate was collected by filtration, washed with ethyl acetate, and dried to give 7β-[2-(2-amino-5-chlorothiazol-4-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylic acid (188 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-e8bb8fb24c04427992b6568c8e5e3330
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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