Anisole → HCID 53799751, compound

HRID 1583871Notes

Reaction equation

HRID 1583871 reaction equation
C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[C:25]1[S:29][C:28]([C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)=[N:27][CH:26]=1)[CH:20]([NH:36][C:37](=[O:67])[C:38](=[N:64][O:65][CH3:66])[C:39]1[N:40]=[C:41]([NH:44]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:42][CH:43]=1)[C:19]2=[O:68])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1>C(O)=O>[NH2:44][C:41]1[S:42][CH:43]=[C:39]([C:38](=[N:64][O:65][CH3:66])[C:37]([NH:36][CH:20]2[C:19](=[O:68])[N:18]3[CH:21]2[S:22][CH2:23][C:24]([C:25]2[S:29][C:28]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)=[N:27][CH:26]=2)=[C:17]3[C:15]([OH:16])=[O:14])=[O:67])[N:40]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 53765200HCID 53765200, compound

Product 1

HCID 53799751HCID 53799751, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The syn isomer of 2-benzhydryloxycarbonyl-7[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-3-[2-(pyridin-3-yl)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1.1 g) is treated with formic acid (20 cc) containing anisole (2 cc) for 30 minutes at 50° C. and the reaction mixture is then concentrated to dryness under reduced pressure (1 mm Hg; 0.13 kPa) at 40° C. The residue is taken up in ethanol (20 cc), which is evaporated off under reduced pressure (30 mm Hg; 4 kPa) at 40° C.; this operation is repeated a further 2 times. The residue is solidified with ethanol (150 cc). The solid is filtered off, washed with ethanol (2×5 cc) and ethyl ether (3×20 cc) and dried to give the syn isomer of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-8-oxo-3-[2-(pyridin-3-yl)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.56 g) in the form of a pale yellow solid.

Workup

  1. concentrationthe reaction mixture is then concentrated to dryness under reduced pressure (1 mm Hg; 0.13 kPa) at 40° C
  2. customwhich is evaporated off under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  3. filtrationThe solid is filtered off
  4. washwashed with ethanol (2×5 cc) and ethyl ether (3×20 cc)
  5. customdried

Sources & evidence

ORD record
ord-826c43cf96f049fab30476350f709ab9
Source dataset
uspto-grants-1985_11
Patent number
US04554350

Reaction notes

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