Phosphate → HCID 15980307, compound

HRID 1158845Notes

Reaction equation

HRID 1158845 reaction equation
[N+](C1C=CC(C[C:9]2[S:15][CH:14]3[N:11]([C:12](=[O:38])[C:13]3([CH:17](OC(=O)C)[C:18]3[S:26][C:25]4[CH2:24][CH2:23][N:22]([CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH2:21][C:20]=4[CH:19]=3)Br)[C:10]=2[C:39]([O-:41])=[O:40])=CC=1)([O-])=O.P([O-])([O-])([O-])=O>C1COCC1.C(#N)C.[Zn]>[CH2:27]([N:22]1[CH2:23][CH2:24][C:25]2[S:26][C:18](/[CH:17]=[C:13]3\[C@@H:14]4[N:11]([C:12]\3=[O:38])[C:10]([C:39]([OH:41])=[O:40])=[CH:9][S:15]4)=[CH:19][C:20]=2[CH2:21]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 2

HCID 1061PhosphateHCID 68455954HCID 68455954, compound

Product 1

HCID 15980307HCID 15980307, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzy-6-[(acetyloxy)(5-benzyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (450 mg, 0.65 mmol) was dissolved in THF (20 mL) and acetonitrile (10 mL). Freshly activated Zn dust (5.2 g) was added rapidly with 0.5 M phosphate buffer (pH 6.5, 28 mL). The reaction vessel was covered with foil to exclude light. The reaction mixture was vigorously stirred for 2 hours at room temperature. The reaction mixture was filtered, cooled to 3° C., and 0.1 M NaOH was added to adjust pH to 8.5. The filtrate was washed with ethyl acetate and the aqueous layer was separated. The aqueous layer was concentrated under high vacuum at 35° C. to give yellow precipitate. The product was purified by HP21 resin reverse phase column chromatography. Initially the column was eluted with deionized water (2 lits) and latter with 10% CAN:Water. The fractions containing the product were collected and concentrated at reduced pressure at room temperature. The yellow solid was washed with acetone and filtered. Dried. Yield: 50 mg, 18%; as yellow crystals; mp. 198° C.; (M+H) 411.

Workup

  1. filtrationThe reaction mixture was filtered
  2. temperaturecooled to 3° C.
  3. addition0.1 M NaOH was added
  4. washThe filtrate was washed with ethyl acetate
  5. customthe aqueous layer was separated
  6. concentrationThe aqueous layer was concentrated under high vacuum at 35° C.
  7. customto give yellow precipitate
  8. customThe product was purified by HP21 resin reverse phase column chromatography
  9. washInitially the column was eluted with deionized water (2 lits) and latter with 10% CAN
  10. additionThe fractions containing the product
  11. customwere collected
  12. concentrationconcentrated at reduced pressure at room temperature
  13. washThe yellow solid was washed with acetone
  14. filtrationfiltered
  15. customDried

Sources & evidence

ORD record
ord-8c6ef05cc7ab4ea792352f017e47c612
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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