1,2-Dichloroethane → (S)-3-((R)-4-Benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

HRID 41069

Reaction equation

HRID 41069 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@@H:16]([CH2:21][CH:22]=[CH2:23])[CH2:17][C:18]([OH:20])=O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52][NH2:53])=[CH:50][CH:49]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@@H:16]([CH2:21][CH:22]=[CH2:23])[CH2:17][C:18]([NH:53][CH2:52][C:51]1[CH:54]=[CH:55][C:48]([Cl:47])=[CH:49][CH:50]=1)=[O:20])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 660364-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 25109988(S)-3-((R)-4-Benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid

Product 1

HCID 25109989(S)-3-((R)-4-Benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamideYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of compound 3a (0.402 g, 1.3 mmol), EDC (0.364 g, 1.9 mmol), HOBT (0.256 g, 1.9 mmol), and Hunig's base (0.662 mL, 3.8 mmol) in dichloromethane (17 mL) was cooled to 0° C. and stirred for half an hour. To this solution 4-chlorobenzylamine (0.174 mL, 1.43 mmol) and a catalytic amount of DMAP were added. The reaction was stirred overnight and the reaction progress was monitored by TLC. The dichloromethane was removed in vacuo and the reaction mixture quenched with aqueous NH4Cl. The solution was washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give well formed white crystals of 4a (0.443 g, 79%). 1H NMR (500 MHz, CDCl3): δ ppm 7.31-7.36 (m, 2H) 7.21-7.29 (m, 5H) 7.17-7.21 (m, 2H) 6.09 (t, J=5.6 Hz, 1H) 5.73-5.82 (m, 1H) 5.04-5.10 (m, 2H) 4.65 (ddd, J=13.3, 6.7, 3.4 Hz 1H) 4.41 (dd, J=15.2, 5.9 Hz, 1H) 4.34 (dd, J=14.9, 5.9 Hz, 1H) 4.23-4.30 (m, 1H) 4.23-4.30 (m, 1H) 4.14-4.18 (m, 2H) 3.28 (dd, J=13.7, 2.9 Hz, 1H) 2.66-2.80 (m, 2H) 2.41-2.51 (m, 2H) 2.22-2.29 (m, 1H); 13C NMR (126 MHz, CDCl3): δ 175.1, 171.0, 153.4, 137.1, 135.7, 134.8, 133.4, 129.7, 129.3, 129.1, 129.0, 127.5, 118.1, 66.3, 55.7, 43.1, 40.1, 38.0, 37.8, 36.3. HRMS calcd. for C24H25ClN2O4 (M+H) m/z 441.1581, found 441.1581.

Workup

  1. stirringThe reaction was stirred overnight
  2. customThe dichloromethane was removed in vacuo
  3. customthe reaction mixture quenched with aqueous NH4Cl
  4. washThe solution was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee9d6e8dca0c49aa84a82ff32de7bcab
Source dataset
uspto-grants-2013_09
Patent number
US08530456B2

Linked notes

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