Sodium Hydroxide → 3-(1,3,4-Thiadiazol-2-yl)thiomethyl-7-[2-hydroxy-2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)-acetamido]-3-cephem-4-carboxylic acid

HRID 1659416Notes

Reaction equation

HRID 1659416 reaction equation
C(OC(NC1SC=C(C(=O)C(NC2C(=O)N3C(C(O)=O)=CCS[C@H]23)=O)N=1)=O)(CC)(C)C.[S:32]1[CH:36]=[N:35][N:34]=[C:33]1[S:37][CH2:38][C:39]1[CH2:40][S:41][C@@H:42]2[CH:49]([NH:50][C:51](=[O:68])[C:52]([C:54]3[NH:55][C:56](=[N:59][C:60]([O:62][C:63]([CH2:66][CH3:67])([CH3:65])[CH3:64])=[O:61])[S:57][CH:58]=3)=[O:53])[C:48](=[O:69])[N:43]2[C:44]=1[C:45]([OH:47])=[O:46].[OH-].[Na+].[BH4-].[Na+]>CO.O>[S:32]1[CH:36]=[N:35][N:34]=[C:33]1[S:37][CH2:38][C:39]1[CH2:40][S:41][C@@H:42]2[CH:49]([NH:50][C:51](=[O:68])[CH:52]([OH:53])[C:54]3[N:55]=[C:56]([NH:59][C:60]([O:62][C:63]([CH2:66][CH3:67])([CH3:65])[CH3:64])=[O:61])[S:57][CH:58]=3)[C:48](=[O:69])[N:43]2[C:44]=1[C:45]([OH:47])=[O:46]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 1317125707-[2-(2-Tert-pentyloxycarbonylamino-1,3-thiazol4-yl)glyoxylamido]-3-cephem-4-carboxylic acidHCID 178447170HCID 178447170, compound

Product 1

HCID 704900353-(1,3,4-Thiadiazol-2-yl)thiomethyl-7-[2-hydroxy-2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)-acetamido]-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(1,3,4-thiadiazol-2-yl)thiomethyl)-7-[2-(2-tert-pentyloxycarbonylamino-1,3-thiazol4-yl)glyoxylamido]-3-cephem-4-carboxylic acid, which can be represented as 3-(1,3,4-thiadiazol-2-yl)thiomethyl-7-[2-(2-tert-pentyloxycarbonylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid, (3.1 g.) in methanol (30 ml.) was added 1 N sodium hydroxide aqueous solution (5.2 ml.) under ice-cooling and stirring. To the mixture was dropwise added a solution of sodium borohydride (0.074 g.) in water (2 ml.) over 10 minutes, and the mixture was stirred for 30 minutes at the same temperature. After the reaction, the reaction mixture was concentrated under reduced pressure. To the residue were added water and ethyl acetate, and the aqueous layer was separated. The aqueous layer was adjusted to pH 5 to 6 with 10% hydrochloric acid and then washed with ethyl acetate. To the aqueous layer was added ethyl acetate, and the mixture was adjusted to pH 1 to 2 with 10% hydrochloric acid. The ethyl acetate layer was separated, washed with water, dried over magnesium sulfate and then treated with activated charcoal. After distillation of the solvent from the ethyl acetate layer, the remaining residue was pulverized in diethyl ether, collected by filtration and then dried to give pale yellow powder of 3-(1,3,4-thiadiazol-2-yl)thiomethyl-7-[2-hydroxy-2-(2-tert-pentyloxycarbonylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid, which can be represented as 3-(1,3,4-thiadiazol-2-yl)thiomethyl-7-[2-hydroxy-2-(2-tert-pentyloxycarbonylimino-2,3-dihydro-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acidc (2.2 g.).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes at the same temperature
  3. customAfter the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionTo the residue were added water and ethyl acetate
  6. customthe aqueous layer was separated
  7. washwashed with ethyl acetate
  8. additionTo the aqueous layer was added ethyl acetate
  9. customThe ethyl acetate layer was separated
  10. washwashed with water
  11. dry with materialdried over magnesium sulfate
  12. additiontreated with activated charcoal
  13. distillationAfter distillation of the solvent from the ethyl acetate layer
  14. filtrationcollected by filtration
  15. customdried

Sources & evidence

ORD record
ord-dc84d0b41a294fec94fc7cf6f4453ba0
Source dataset
uspto-grants-1981_12
Patent number
US04303655

Reaction notes

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