Ethyl Acetate → HCID 9900773, compound

HRID 2289207Notes

Reaction equation

HRID 2289207 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>[CH2:1]([O:3][C:4]([C@H:5]1[O:22][C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][C@H:6]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:23])[CH3:2]

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

Conditions

Temperature
2 °C

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-752ee54afb8f4e08ad6d2cb2f49cd358
Source dataset
uspto-grants-2000_07
Patent number
US06090951

Reaction notes

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