Water → 3-Acetonyl-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 463589Notes

Reaction equation

HRID 463589 reaction equation
[CH2:1]([C:5]1[CH2:12][S:11][CH:10]2[N:7]([C:8](=[O:45])[CH:9]2[NH:13][C:14](=[O:44])[C:15](=[N:41][O:42][CH3:43])[C:16]2[N:17]=[C:18]([NH:21]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:19][CH:20]=2)[C:6]=1[C:46]([O:48]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:47])[C:2]([CH3:4])=[O:3].O>C(O)=O>[CH2:1]([C:5]1[CH2:12][S:11][CH:10]2[N:7]([C:8](=[O:45])[CH:9]2[NH:13][C:14](=[O:44])[C:15]([C:16]2[N:17]=[C:18]([NH2:21])[S:19][CH:20]=2)=[N:41][O:42][CH3:43])[C:6]=1[C:46]([OH:48])=[O:47])[C:2]([CH3:4])=[O:3]

Participants

4

Reactant 2

HCID 962WaterHCID 544195633-Acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 540529953-Acetonyl-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-eneYield 51.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A solution of the syn isomer of 3-acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (4.5 g) in formic acid (42 cc) is heated to 50° C. Distilled water (15 cc) is added in the course of 15 minutes and the mixture is stirred for 15 minutes at 50° C. It is filtered and the filtrate is concentrated to dryness under reduced pressure (1 mm Hg; 0.13 kPa) at 20° C. The residue is taken up 3 times in succession with ethanol (50 cc), which is evaporated off to dryness each time under reduced pressure (1 mm Hg; 0.13 kPa) at 20° C. The solid residue is recrystallised from propan-2-ol (60 cc) and the crystals are filtered off, washed with diethyl ether (20 cc) and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 30° C. This yields the syn isomer of 3-acetonyl-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.2 g) in the form of beige crystals.

Workup

  1. filtrationIt is filtered
  2. concentrationthe filtrate is concentrated to dryness under reduced pressure (1 mm Hg; 0.13 kPa) at 20° C
  3. customis evaporated off to dryness each time under reduced pressure (1 mm Hg; 0.13 kPa) at 20° C
  4. customThe solid residue is recrystallised from propan-2-ol (60 cc)
  5. filtrationthe crystals are filtered off
  6. washwashed with diethyl ether (20 cc)
  7. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 30° C

Sources & evidence

ORD record
ord-a0b45a1d1b774fac9b56dffea5009734
Source dataset
uspto-grants-1985_05
Patent number
US04520193

Reaction notes

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