Benzyl chloroformate → HCID 10785316, compound

HRID 1637904Notes

Reaction equation

HRID 1637904 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH:7]=[N:8][C@H:9]([C:13]([O-:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[CH:5][CH:4]=1.[Na+].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>>[CH2:23]([O:22][C:20]([N:8]1[C@@H:9]([CH:10]([CH3:12])[CH3:11])[C:13](=[O:15])[O:14][C@H:7]1[C:6]1[CH:16]=[CH:17][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 10387Benzyl chloroformateHCID 70299797HCID 70299797, compound

Product 1

HCID 10785316HCID 10785316, compound

Procedure

(2S,4S)-N-Benzyloxycarbonyl4-isopropyl-2-(4'-methoxyphenyl)-1,3-oxazolidin-5-one (22) was prepared from sodium N-(para-methoxybenzylidene)-(L)-valinate (2.57 g, 10.0 mM) and benzyl chloroformate (1.43 mL, 10.0 mM) following general procedure C and obtained as a colourless oil after purification by flash column chromatography, using 25% ethyl acetate/petrol as eluant (2.54 g, 69% mixture of 2 rotamers in a ratio of 2:1, NMR data for major isomer only reported): IR (CHCl3): 1795, 1715 cm-1 ; 1H NMR (200 MHz, CDCl3): δ 6.92-7.41 (m, 9H), 6.87 (s, 1H), 5.24 (s, 2H), 4.26 (d, J=5 Hz, 1H), 3.82 (s, 3H), 1.10-1.35 (m, 1H), 0.94 (d, J=5 Hz, 3H), 0.98 (d, J=5 Hz, 3H); 13C NMR (50.3 MHz, CDCl3): δ 171.2, 160.2, 155.1, 135.3, 129.5, 128.6, 128.0, 127.3, 113.8, 88.4, 68.3, 61.6, 55.3, 31.5, 19.1, 18.4; LRMS (Scan AP+): 370 (MH+); HRMS: calcd for C21H24NO5 (MH+): 370.1654; found: 370.1654.

Workup

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

Sources & evidence

ORD record
ord-adf959050de94cb2bbb3f0e4d6a9625e
Source dataset
uspto-grants-2000_03
Patent number
US06043278

Reaction notes

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