2-Oxazolidinone → Triphosgene
Reaction equation
[NH2:1][C@@H:2]([CH2:11][CH2:12][CH3:13])[CH:3]([OH:10])[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].O1CCNC1=O.[Cl:20][C:21]([Cl:31])([O:23][C:24](=[O:30])[O:25][C:26]([Cl:29])([Cl:28])[Cl:27])[Cl:22]>>[NH2:1][C@@H:2]([CH2:11][CH2:12][CH3:13])[C@H:3]([OH:10])[C:4]([NH:6][CH:7]1[CH2:8][CH2:9]1)=[O:5].[Cl:20][C:21]([Cl:22])([O:23][C:24](=[O:30])[O:25][C:26]([Cl:29])([Cl:27])[Cl:28])[Cl:31]Participants
Procedure
(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamide was converted to the corresponding oxazolidinone by reaction with triphosgene. The resulting product was analyzed by proton NMR and the stereochemistry of the product was determined by the coupling constants (J value) for the protons at C-4 and C-5 of the cyclized derivatives. Based on literature values for similar products (Tsuda, M.; Muraoka, Y.; Nagai, M.; Aoyagi, T.; Takeuchi, T. J. Antibiotics 1996, 49, 281-286, Herranz, R.; Castro-Pichel, J.; Vinuesa, S.; Garcia-López. M. T. J. Org. Chem. 1990, 55, 2232, Williams, T. M.; Crumbie, R.; Mosher, H. S. J. Org. Chem. 1985, 50, 91-97), the cis-isomer (J4,5=8.8 Hz) was obtained exclusively from the reaction of (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide with triphosgene, indicating that the absolute configuration of (3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide was (2S,3S).
Sources & evidence
- ORD record
- ord-2f1c35ddb46d4142850d8db6f72f91b0
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143448B2
Reaction notes
Loading…