Carbamate → (1-Benzyl-2-hydroxy-3-{3-[4-phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]-piperidine-1-yl}-propyl)-carbamic acid tert-butyl ester

HRID 720884Notes

Reaction equation

HRID 720884 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29](=[O:32])([O-:31])[NH2:30].[CH:33]([OH:36])([CH3:35])[CH3:34]>>[C:14]([O:32][C:29](=[O:31])[NH:30][CH:34]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:33]([OH:36])[CH2:35][N:25]1[CH2:26][CH2:27][CH2:28][CH:23]([C:21](=[O:22])[NH:20][CH:10]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:24]1)([CH3:19])([CH3:13])[CH3:15]

Participants

4

Reactant 3

HCID 276CarbamateHCID 3776IsopropanolHCID 12020263Piperidine-3-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Product 1

HCID 18727510(1-Benzyl-2-hydroxy-3-{3-[4-phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]-piperidine-1-yl}-propyl)-carbamic acid tert-butyl ester

Conditions

Temperature
70 °C

Procedure

Piperidine-3-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (13) (150 mg; 0.4 mmol) is dissolved in isopropanol (10 mL) at ambient temperature. tert-Butyl[S-(R*, R*)]-(−)-(1-oxiranyl)-2-phenylethyl)carbamate (104.4 mg; 0.4 mmol) is added, then the mixture is heated to 70° C. and maintained for 18 hours. After cooling to ambient temperature, the solution is concentrated in vacuo at 40° C. The residue is purified via silica gel chromatography with gradient elution (1%→20% methanol in methylene chloride) affording the desired product (166.7 mg) as an oil. ESMS:MH+ 642.6 (base).

Workup

  1. temperaturemaintained for 18 hours
  2. temperatureAfter cooling to ambient temperature
  3. concentrationthe solution is concentrated in vacuo at 40° C
  4. customThe residue is purified via silica gel chromatography with gradient elution (1%→20% methanol in methylene chloride)

Sources & evidence

ORD record
ord-48451de1c0ac4e84a993a8f8815f5334
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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