p-Toluenesulfonic acid → HCID 10998777, compound

HRID 1637896Notes

Reaction equation

HRID 1637896 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([CH:10]([CH3:11])[CH3:12])[C:13](=[O:15])[O:14][CH2:16]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 83693Boc-L-Valine

Product 1

HCID 10998777HCID 10998777, compound

Procedure

(4S)-N-tert-Butyloxycarbonyl4-isopropyl-1,3-oxazolidin-5-one (3) was prepared from N-tert-butyloxycarbonyl-(L)-valine (2.17 g, 10.0 mM) and para-toluenesulfonic acid (30 mg) following general procedure A and obtained as a white solid after crystallisation from chloroform (1.67 g, 73%): [a]D20 +104.9 (c 1, CHCl3); mp 43-45° C.; IR (KBr): 1795, 1705 cm-1 ; 1H NMR (200 MHz, CDCl3): 67 5.55 (br, 1H), 5.10 (d, J=4 Hz, 1H), 4.15 (d, J=4 Hz, 1H), 2.21-2.43 (m, 1H), 1.49 (s, 9H), 1.06 (d, J=7 Hz, 3H), 1.02 (d, J=7 Hz, 3H); 13C NMR (50.3 MHz, CDCl3): d 171.8, 152.6, 81.6, 78.4, 59.9, 31.1, 27.9, 17.9, 17.5; LRMS (NH3): 230 (MH+). Anal. Calcd for C11H19NO4 : C, 57.63; H, 8.35; N, 6.11; found: C, 57.62; H, 8.54; N, 5.93.

Workup

  1. customobtained as a white solid
  2. customafter crystallisation from chloroform (1.67 g, 73%)

Sources & evidence

ORD record
ord-f963fe2289b5499da3e71396d205b85d
Source dataset
uspto-grants-2000_03
Patent number
US06043278

Reaction notes

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