1,2-Dichloroethane → 3-(2-Benzylaminocarbonyl-4-benzyloxy-phenyl)-acrylic acid tert-butyl ester

HRID 1181108Notes

Reaction equation

HRID 1181108 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:18]=[CH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:13]([CH:17]=1)[C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:23]([O:22][C:20](=[O:21])[CH:19]=[CH:18][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:17][C:13]=1[C:14]([NH:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:16])([CH3:25])([CH3:24])[CH3:26]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 69232261HCID 69232261, compound

Product 1

HCID 692309383-(2-Benzylaminocarbonyl-4-benzyloxy-phenyl)-acrylic acid tert-butyl esterYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-benzyloxy-2-(2-tert-butoxycarbonyl-vinyl)-benzoic acid (1.45 g, 4.09 mmol) in CH2Cl2 (40 mL) was added benzylamine (0.613 g, 5.73 mmol), EDC (1.254 g, 6.54 mmol), and DMAP (1.00 g, 8.18 mmol). The resulting mixture was stirred at room temperature for 12 h, washed with aqueous NH4Cl (50 mL), and extracted with CH2Cl2 (2×50 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was then purified using silica gel chromatography (hexanes/EtOAc 8/2) to afford the title compound as an oil (720 mg, 40%). 1H NMR (400 MHz, CDCl3): δ 1.52 (s, 9H), 4.63 (d, 2H, J=5.5 Hz), 5.09 (s, 2H), 5.97 (br s, 1H), 6.22 (d, 1H, J=15.6 Hz), 7.01 (dd, 1H, J=2.7, 8.6 Hz), 7.10 (d, 1H, J=2.8 Hz), 7.28-7.42 (m, 10H), 7.55 (d, 1H, J=9.0 Hz), 7.88 (d, 1H, J=16.0 Hz).

Workup

  1. washwashed with aqueous NH4Cl (50 mL)
  2. extractionextracted with CH2Cl2 (2×50 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was then purified

Sources & evidence

ORD record
ord-538107d3fec1407684dd9f50aceb9e8a
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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