Hydrochloric Acid → HCID 68503992, compound

HRID 1176212Notes

Reaction equation

HRID 1176212 reaction equation
Cl[C:2](OC1C=CC=CC=1)=[O:3].[NH2:11][C:12]1[CH:13]=[C:14]([CH:50]=[CH:51][C:52]=1[OH:53])[CH2:15][O:16][CH:17]1[CH:22]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])=[CH:25][CH:24]=2)[CH2:21][CH2:20][N:19]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:18]1.C(=O)([O-])O.[Na+].[OH-].[Na+].Cl>CO.O>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[CH2:34][O:33][CH2:32][CH2:31][CH2:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C@H:22]2[CH2:21][CH2:20][N:19]([C:43]([O:45][C:46]([CH3:49])([CH3:47])[CH3:48])=[O:44])[CH2:18][C@@H:17]2[O:16][CH2:15][C:14]2[CH:50]=[CH:51][C:52]3[O:53][C:2](=[O:3])[NH:11][C:12]=3[CH:13]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 68501582HCID 68501582, compound

Product 1

HCID 68503992HCID 68503992, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

0.133 ml of phenyl chloroformate are added dropwise to the stirred emulsion of 0.640 g of tert-butyl 3-(3-amino-4-hydroxybenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 0.086 g of sodium hydrogencarbonate in 4 ml of methanol and 4 ml of water. The reaction mixture is stirred over 15 minutes and then admixed with 2 ml of methanol. After a further 15 minutes, it is admixed with 0.51 ml of 2N NaOH. After a further 10 minutes, the mixture is admixed with 20 ml of 0.5N HCl and extracted with tert-butyl methyl ether (2×30 ml). The organic phases are washed successively with water (30 ml) and brine (30 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.52 (3:1 EtOAc-heptane); Rt=5.56.

Workup

  1. waitAfter a further 15 minutes
  2. waitAfter a further 10 minutes
  3. extractionextracted with tert-butyl methyl ether (2×30 ml)
  4. washThe organic phases are washed successively with water (30 ml) and brine (30 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ee33e452836f4170b426fa52dc31da3d
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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