Potassium Carbonate → HCID 53656359, compound

HRID 1193489Notes

Reaction equation

HRID 1193489 reaction equation
Cl[C@H:2]([CH3:19])[C:3]([O:5][CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[OH:20]/[N:21]=[C:22](/[C:29]1[N:30]=[C:31]([NH:34][C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[S:32][CH:33]=1)\[C:23]([O:25]CC=C)=[O:24].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:35]([NH:34][C:31]1[S:32][CH:33]=[C:29]([C:22](=[N:21][O:20][C@H:2]([C:3]([O:5][CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])[CH3:19])[C:23]([OH:25])=[O:24])[N:30]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14402821HCID 14402821, compoundHCID 14524946HCID 14524946, compound

Product 1

HCID 53656359HCID 53656359, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 11 ml of dimethylformamide was dissolved 2.16 g of benzhydryl L-lactate. After cooling the solution to -40° C., 0.8 ml of sulfuryl chloride was added thereto followed by stirring for an hour. Thereafter the reaction solution was extracted with ethyl acetate and a sodium bicarbonate aqueous solution. The organic phase was washed with water, dried and then concentrated to dryness to give 1.8 g of benzhydryl (2R)-2-chloropropionate. This ester was reacted with 3.1 g of allyl (Z)-2-hydroxyimino-2-(2-tritylaminothiazol-4-yl)acetate prepared in a manner similar to the description of Published Unexamined Japanese Patent Application No. 149289/80 in 16 ml of dimethylsulfoxide overnight at room temperature in the presence of 1.8 g of potassium carbonate. The reaction solution was partitioned with ice water and ethyl acetate. The organic phase was washed with water, dried and concentrated. The residue was dissolved in 30 ml of methylene chloride. To the solution were added 182 mg of triphenylphosphine and 34 mg of tetrakistriphenylphosphine palladium. The mixture was stirred at room temperature for 30 minutes. Then, a solution of 1.26 g of potassium 2-ethylhexanoate in ethyl acetate. After stirring at room temperature for 2 hours, 45 ml of isopropyl ether was added and the mixture was allowed to stand overnight at 0° C. The obtained precipitates were partitioned in ethyl acetate-acidic water (pH 2.8). The organic phase was washed with water, dried and concentrated to give 2.13 g of 2-(2-tritylamino-thiazol-4-yl)-2-{(1S)-1-diphenylmethoxycarbonylethoxyimino}acetic acid.

Workup

  1. customprepared in a manner similar to the description of Published Unexamined Japanese Patent Application No
  2. customovernight
  3. customat room temperature
  4. customThe reaction solution was partitioned with ice water and ethyl acetate
  5. washThe organic phase was washed with water
  6. customdried
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in 30 ml of methylene chloride
  9. additionTo the solution were added 182 mg of triphenylphosphine and 34 mg of tetrakistriphenylphosphine palladium
  10. stirringAfter stirring at room temperature for 2 hours
  11. addition45 ml of isopropyl ether was added
  12. waitto stand overnight at 0° C
  13. customThe obtained precipitates
  14. customwere partitioned in ethyl acetate-acidic water (pH 2.8)
  15. washThe organic phase was washed with water
  16. customdried
  17. concentrationconcentrated

Sources & evidence

ORD record
ord-f03f59f28939477282594af227b8fd4a
Source dataset
uspto-grants-1989_03
Patent number
US04810702

Reaction notes

Loading…