Benzyl chloroformate → HCID 21967713, compound

HRID 1637898Notes

Reaction equation

HRID 1637898 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH:7]=[N:8][C@H:9]([C:17]([O-:19])=[O:18])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[Na+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>>[CH2:10]([C@H:9]1[C:17](=[O:19])[O:18][C@@H:7]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:21][CH:20]=2)[N:8]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 10387Benzyl chloroformateHCID 70301298HCID 70301298, compound

Product 1

HCID 21967713HCID 21967713, compound

Procedure

(2S,4S)-4-Benzyl-N-benzyloxycarbonyl-2-(4'-methoxyphenyl)-1,3-oxazolidin-5-one (13) was prepared from sodium N-(para-methoxybenzylidene)-(L)-phenylalaninate (3.05 g, 10.0 mM) and benzyl chloroformate (1.43 mL, 10.0 mM) following general procedure C and obtained as a white solid after crystallisation from diethyl ether (2.87 g, 69%): [α]D20 +50.1 (c 1.0, CHCl3); mp 85° C.; IR (KBr): 1795, 1700 cm-1 ; 1H NMR (500 MHz, d8 -toluene, 90° C.): δ 6.49-7.08 (m, 14H), 6.04 (s, 1H), 4.92 (d, J=12 Hz, 1H), 4.83 (d, J=12 Hz, 1H), 4.19 (dd, J=4, 6 Hz, 1H), 3.39 (s, 3H), 3.25 (dd, J=6, 14 Hz, 1H), 3.08 (dd, J=4, 14 Hz, 1H); 13C NMR (50.3 MHz, CDCl3): δ 171.4, 160.3, 151.5, 135.3, 129.2, 128.8, 128.5, 128.2, 127.3, 113.4, 89.3, 67.8, 58.4, 55.3, 34.5; LRMS (EI): 418 (MH+). Anal. Calcd for C25H23NO5 : C, 71.93; H, 5.55; N, 3.35. Found: C, 72.22; H, 5.36; N, 3.28.

Workup

  1. customobtained as a white solid
  2. customafter crystallisation from diethyl ether (2.87 g, 69%)

Sources & evidence

ORD record
ord-3a68a5544da94a8e86454a3c43e71276
Source dataset
uspto-grants-2000_03
Patent number
US06043278

Reaction notes

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