p-Toluenesulfonic acid → HCID 12084899, compound

HRID 1637895Notes

Reaction equation

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

Participants

Reactant 2

HCID 6101p-Toluenesulfonic acid

HCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 12084899HCID 12084899, compound

Procedure

(4S)-N-tert-Butyloxycarbonyl4-methyl-1,3-oxazolidin-5-one (2) was prepared from N-tert-butyloxycarbonyl-(L)-alanine (1.89 g, 10.0 mM) and para-toluenesulfonic acid (30 mg) following general procedure A and obtained as fine white needles after crystallisation from chloroform (1.49 g, 74%): [α]D20 +78.1 (c 1, CHCl3); mp 64-67° C.; IR (KBr) 1795, 1705 cm-1 ; 1H NMR (200 MHz, CDCl3): δ 5.40 (d, J=2 Hz, 1H), 5.20 (d, J=2 Hz, 1H), 4.50 (q, J=7 Hz, 1H), 1.55 (d, J=7 Hz, 3H), 1.45 s (s, 9H); 13C NMR (50.3 MHz, CDCl3): δ 173.5, 152.0, 81.4, 77.3, 50.3, 27.8, 16.3; LRMS (NH3): 219 (MNH4+). Anal. Calcd for C9H15NO4 : C, 53.72; H, 7.51; N, 6.96; found: C, 53.58; H, 7.71; N, 6.70.

Workup

customobtained as fine white needles
customafter crystallisation from chloroform (1.49 g, 74%)

Sources & evidence

ORD record: ord-16e3b40c2cda49189dc5d06338b39a60
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043278

Reaction notes

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