1,2-Dichloroethane → tert-butyl[(R)-2-(4-butyryl-4-cyclohexylpiperidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate

HRID 1855656Notes

Reaction equation

HRID 1855656 reaction equation
[CH:1]1([C:7]2([C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]([O:22][C:23]([NH:25][C@H:26]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:27](O)=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:13]([C:7]1([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:8][CH2:9][N:10]([C:27](=[O:28])[C@H:26]([NH:25][C:23](=[O:24])[O:22][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[CH2:11][CH2:12]1)(=[O:17])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7017908Boc-O-methyl-D-tyrosineHCID 669878491-(4-Cyclohexylpiperidin-4-yl)butan-1-one

Product 1

HCID 86659316tert-butyl[(R)-2-(4-butyryl-4-cyclohexylpiperidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamateYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.44 g (1.9 mmol) of 1-(4-cyclohexylpiperidin-4-yl)butan-1-one, 0.56 g of (R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid (1.9 mmol), 0.4 g (2.1 mmol) of EDC and 0.282 g (2.1 mmol) of HOBt are dissolved in 4 ml of DMF. The mixture is stirred at room temperature for 2 hours. The solution is washed with aqueous 2.5% citric acid solution and extracted with ethyl acetate, and the organic phase is then washed with aqueous 10N sodium hydroxide solution. It is dried over sodium sulfate, filtered and concentrated. The crude product obtained is chromatographed on silica gel (eluent: 7/3 heptane/ethyl acetate). 0.43 g is obtained in the form of a colourless oil in a yield of 44%.

Workup

  1. washThe solution is washed with aqueous 2.5% citric acid solution
  2. extractionextracted with ethyl acetate
  3. washthe organic phase is then washed with aqueous 10N sodium hydroxide solution
  4. dry with materialIt is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7e2326430e7a42dfb3cd69182713f9b2
Source dataset
uspto-grants-2015_02
Patent number
US08962846B2

Reaction notes

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