Trifluoroacetic acid → (7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 2214768Notes

Reaction equation

HRID 2214768 reaction equation
FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C1(C([O:28][C:29]([C:31]2[N:32]3[CH:35]([CH2:36][CH2:37][C:38]=2[S:39][C:40]2[S:41][C:42]([NH2:45])=[N:43][N:44]=2)[C@@H:34]([NH:46][C:47](=[O:77])/[C:48](/[C:70]2[N:71]=[C:72]([NH2:76])[S:73][C:74]=2[Cl:75])=[N:49]\[O:50]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:33]3=[O:78])=[O:30])C2C=CC=CC=2)C=CC=CC=1>ClCCl>[NH2:76][C:72]1[S:73][C:74]([Cl:75])=[C:70](/[C:48](=[N:49]/[OH:50])/[C:47]([NH:46][C@H:34]2[C:33](=[O:78])[N:32]3[CH:35]2[CH2:36][CH2:37][C:38]([S:39][C:40]2[S:41][C:42]([NH2:45])=[N:43][N:44]=2)=[C:31]3[C:29]([OH:30])=[O:28])=[O:77])[N:71]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 140482355benzhydryl (7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-3-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 141612336(7R)-7-[[(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of trifluoroacetic acid (10 mL), triethylsilane (5 mL) and dichloromethane (10 mL) was cooled to 0° C. and (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino]acetamido]-3-[5-amino-1,3,4-thiadiazol-2-ylthio]-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate diphenylmethyl ester from the previous step (2.3 g) was added in portions. The reaction mixture was stirred for 3 hours at 0° C., allowed to warm up to room temperature and evaporated to dryness. The residue was treated with diethyl ether (50 mL) and the solid that formed was filtered and dried to give 2.4 g of crude product. The crude product was purified on HP 20 initially with water elution until the pH was neutral, after which the product was eluted with acetonitrile:water 80:20. The solvent was evaporated to give the 0.65 g of the title compound.

Workup

  1. temperatureto warm up to room temperature
  2. customevaporated to dryness
  3. additionThe residue was treated with diethyl ether (50 mL)
  4. customthe solid that formed
  5. filtrationwas filtered
  6. customdried
  7. customto give 2.4 g of crude product
  8. customThe crude product was purified on HP 20 initially with water elution until the pH
  9. washafter which the product was eluted with acetonitrile:water 80:20
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-71e28d17b7d5428387ced79d7899faaa
Source dataset
uspto-grants-2006_09
Patent number
US07109190B2

Reaction notes

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