Trifluoroacetic acid → HCID 178527013, compound

HRID 1091009Notes

Reaction equation

HRID 1091009 reaction equation
C1(C([O:14][C:15]([C:17]2[N:18]3[CH:21]([CH2:22][CH2:23][C:24]=2[P:25](OCC)(OCC)=[O:26])[CH:20]([NH:33][C:34](=[O:43])[CH2:35][O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:19]3=[O:44])=[O:16])C2C=CC=CC=2)C=CC=CC=1.Br[Si](C)(C)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[O:36]([CH2:35][C:34]([NH:33][CH:20]1[C:19](=[O:44])[N:18]2[CH:21]1[CH2:22][CH2:23][C:24]([PH2:25]=[O:26])=[C:17]2[C:15]([OH:16])=[O:14])=[O:43])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 76113BromotrimethylsilaneHCID 544202427-[(Phenoxyacetyl)amino]-8-oxo-3-(diethoxyphosphinyl)-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)ester

Product 1

HCID 178527013HCID 178527013, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-[(phenoxyacetyl)amino]-8-oxo-3-(diethoxyphosphinyl)-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (diphenylmethyl)ester (618 mg, 1 mmol) in methylene chloride (20 mL) was cooled to 0° C. under nitrogen. Bromotrimethylsilane (612 mg, 4 mmol) was added and the stirred reaction warmed to room temperature. After two hours, the solvent was removed in vacuo. The residue was stirred at room temperature with methanol-water for 0.5 hours. The reaction product was concentrated and (1 mmol) of the product was treated with trifluoroacetic acid (10 mL) and triethylsilane (4 mL) and stirred vigorously for one hour. The volatiles were removed in vacuo and the residue purified by flash chromatography on silica gel (21/7/7/9 ethyl acetate/acetonitrile/acetic/acid/water) followed by medium pressure liquid chromatography on a C18 column eluted with 10% to 20% acetonitrile/water. The fractions containing pure product were combined and lyophilized to yield 20 mg (5%) 7-[(phenoxyacetyl)amino]-8-oxo-3-phosphinyl-1-azabicyclo[ 4.2.0]-oct-2-ene-2-carboxylic acid:

Workup

  1. customthe stirred reaction
  2. customthe solvent was removed in vacuo
  3. concentrationThe reaction product was concentrated
  4. stirringstirred vigorously for one hour
  5. customThe volatiles were removed in vacuo
  6. customthe residue purified by flash chromatography on silica gel (21/7/7/9 ethyl acetate/acetonitrile/acetic/acid/water)
  7. washeluted with 10% to 20% acetonitrile/water
  8. additionThe fractions containing pure product

Sources & evidence

ORD record
ord-8ff13471f5da4ca99273b5d09ca094b5
Source dataset
uspto-grants-1992_01
Patent number
US05084447

Reaction notes

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