HCID 57318876, compound → HCID 86739116, compound

HRID 1649268Notes

Reaction equation

HRID 1649268 reaction equation
C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH:25]=[CH:26][S:27][C:28]1[N:33]([CH3:34])[C:32](=[O:35])[C:31](=[O:36])[N:30]([CH2:37][CH:38](OCC)[O:39]CC)[N:29]=1)[CH:20]([NH:45][C:46](=[O:76])[C:47](=[N:73][O:74][CH3:75])[C:48]1[N:49]=[C:50]([NH:53]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:51][CH:52]=1)[C:19]2=[O:77])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O.O>[NH2:53][C:50]1[S:51][CH:52]=[C:48]([C:47](=[N:73][O:74][CH3:75])[C:46]([NH:45][CH:20]2[C:19](=[O:77])[N:18]3[CH:21]2[S:22][CH2:23][C:24]([CH:25]=[CH:26][S:27][C:28]2[N:33]([CH3:34])[C:32](=[O:35])[C:31](=[O:36])[N:30]([CH2:37][CH:38]=[O:39])[N:29]=2)=[C:17]3[C:15]([OH:16])=[O:14])=[O:76])[N:49]=1

Participants

4

Reactant 1

HCID 57318876HCID 57318876, compound

Product 1

HCID 86739116HCID 86739116, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of product (9c) (1.9 g) in formic acid (20 cc) is stirred for 30 minutes at 50° C. and then diluted with water (2 cc) and stirred for 10 minutes at 50° C. After cooling to 20° C., the reaction mixture is filtered and the filtrate is concentrated under reduced pressure (0.1 mm Hg; 0.013 kPa) at 35° C. The residue is triturated with ethanol (20 cc), which is evaporated off under reduced pressure (30 mm Hg; 4 kPa) at 40°. This operation is repeated 3 times and the residue is then taken up in ethanol (30 cc). The solid is isolated on a vacuum filter, washed with ethanol (3×10 cc) and with ethyl ether (3×10 cc) and dried. This yields the E form of the syn isomer of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-3-[2-(5,6 -dioxo-1-formylmethyl-4-methyl-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl)thiovinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (product 9) (0.96 g) in the form of a cream-coloured solid.

Workup

  1. temperatureAfter cooling to 20° C.
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure (0.1 mm Hg; 0.013 kPa) at 35° C
  4. customThe residue is triturated with ethanol (20 cc), which
  5. customis evaporated off under reduced pressure (30 mm Hg; 4 kPa) at 40°
  6. customThe solid is isolated on a vacuum
  7. filtrationfilter
  8. washwashed with ethanol (3×10 cc) and with ethyl ether (3×10 cc)
  9. customdried

Sources & evidence

ORD record
ord-a903f13ec3224e919a6f25b2ab750c37
Source dataset
uspto-grants-1983_11
Patent number
US04415562

Reaction notes

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