benzhydryl (6R)-8-oxo-3-[(Z)-prop-1-enyl]-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate → (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(E)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 2352086Notes

Reaction equation

HRID 2352086 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:58]/[O:59]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:27]([NH:29][CH:30]2[C:56](=[O:57])[N:32]3[C:33]([C:40]([O:42]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:41])=[C:34](/[CH:37]=[CH:38]\[CH3:39])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:58]/[OH:59])/[C:27]([NH:29][CH:30]2[C:56](=[O:57])[N:32]3[C:33]([C:40]([OH:42])=[O:41])=[C:34](/[CH:37]=[CH:38]/[CH3:39])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

3

Reactant 1

HCID 16167558benzhydryl (6R)-8-oxo-3-[(Z)-prop-1-enyl]-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 14052498(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(E)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of the crude product of Example 33 containing 20% of its E isomer (9.2 g, 8.7 mmol) in 85% HCOOH (60 ml) was stirred for 1 hr at room temperature and evaporated in vacuo. The residue was treated with 90%-TFA (60 ml) for 1 hr at room temperature and poured into ice-water (300 ml). The insolubles were filtered off. The filtrate was chromatographed on a reverse phase column (Waters, prepPAK C18, 300 ml) and the column was eluted with 20% MeOH. The polar fractions were combined, concentrated in vacuo and the residue was triturated with isopropyl ether to give 1.15 g (33%) of the Z isomer and the less polar fractions gave 143 mg (4%) of the title compound.

Workup

  1. customevaporated in vacuo
  2. additionThe residue was treated with 90%-TFA (60 ml) for 1 hr at room temperature
  3. additionpoured into ice-water (300 ml)
  4. filtrationThe insolubles were filtered off
  5. customThe filtrate was chromatographed on a reverse phase column (Waters, prepPAK C18, 300 ml)
  6. washthe column was eluted with 20% MeOH
  7. concentrationconcentrated in vacuo
  8. customthe residue was triturated with isopropyl ether
  9. customto give 1.15 g (33%) of the Z isomer

Sources & evidence

ORD record
ord-1fce98b6b3ab49f590141caeb34ad6b8
Source dataset
uspto-grants-1989_10
Patent number
US04874856

Reaction notes

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