Ethyl Acetate → HCID 9900773, compound

HRID 2393922Notes

Reaction equation

HRID 2393922 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C@H:5]([OH:22])[C@H:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].CS(Cl)(=O)=O.CCOC(C)=O.S([O-])(=O)(=O)C>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:9]1([C:8]2[O:22][C@H:5]([C:4]([O:3][CH2:1][CH3:2])=[O:23])[C@H:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 9883276(2R,3S)-3-PHENYLISOSERINE ETHYLESTER

Product 1

HCID 9900773HCID 9900773, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

In a 100 ml flask containing a solution of (2R,3S)-N-benzoyl-3-phenylisoserine ethyl ester (2.00 g, 6.38 mmol) in pyridine (20 ml) at 0° C. was added methanesulfonyl chloride (0.52 ml, 6.70 mmol) dropwise over a 2 minute period. The solution was stirred at 0° to 4° C. for 90 minutes and then at 65°-70° C. for 18 hours. (The reaction was monitored by TLC using 1:2 EtOAc:Toluene as eluent, Rf for the starting material=0.42, Rf for the mesylate=0.48 and Rf for the cis-oxazoline title product=0.78, UV visualization.)

Workup

  1. waitat 65°-70° C. for 18 hours

Sources & evidence

ORD record
ord-81e55cee509b41cca773b1c9946f7042
Source dataset
uspto-grants-1998_09
Patent number
US05808102

Reaction notes

Loading…