p-Toluenesulfonic acid → HCID 15406682, compound

HRID 1637897Notes

Reaction equation

HRID 1637897 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[C:14](=[O:16])[O:15][CH2:17]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 15406682HCID 15406682, compound

Procedure

(4S)-N-tert-Butyloxycarbonyl 4-isobutyl-1,3-oxazolidin-5-one (4) was prepared from N-tert-butyloxycarbonyl-(L)-leucine (2.31 g, 10.0 mM) and para-toluenesulfonic acid (30 mg) following general procedure A and obtained as a colourless, slowly solidifying oil after purification by flash column chromatography, using 30% chloroform/petroleum ether as eluant (1.91 g, 79%): [α] D20 +88.5 (c 0.9, CHCl3); IR (CHCl3): 1790, 1720 cm-1 ; 1H NMR (200 MHz, CDCl3): δ 5.48 (d, J=5 Hz, 1H), 5.09 (d, J=5 Hz, 1H), 4.22 (t, J=6 Hz, 1H), 1.43 (s, 9H), 1.23-1.16 (m, 3H), 0.92 (d, J=5 Hz, 3H), 0.90 (d, J=5 Hz, 3H); 13C NMR (50.3 MHz, CDCl3): δ 172.9, 152.2, 81.5, 77.8, 53.2, 39.4, 27.9, 24.2, 22.4,22.2; LRMS (NH3): 244 (MH+).

Workup

  1. customobtained as a colourless,
  2. customafter purification by flash column chromatography

Sources & evidence

ORD record
ord-1f76208a970a4799968879b8ff78d29b
Source dataset
uspto-grants-2000_03
Patent number
US06043278

Reaction notes

Loading…