Sodium Bicarbonate → HCID 54217083, compound

HRID 1602007Notes

Reaction equation

HRID 1602007 reaction equation
C(O[C:6](=O)[N:7]([C@@H:9]([C:21](=[O:37])[N:22]([C@@H:24]([C:32](=[O:36])[N:33]([CH3:35])[CH3:34])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:23])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)C)(C)(C)C.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.ClCCl>[CH3:35][N:33]([CH3:34])[C:32]([C@H:24]([N:22]([CH3:23])[C:21](=[O:37])[C@H:9]([NH:7][CH3:6])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:36]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 54010185HCID 54010185, compound

Product 1

HCID 54217083HCID 54217083, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of N-((1R)-1-(N-((1R)-1-(dimethylcarbamoyl)-2-phenylethyl)-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylcarbamic acid tert-butylester (6.6 g, 12.8 mmol) in 50% trifluoroacetic acid/dichloromethane (15 ml) was stirred for 10 min. Then saturated sodium bicarbonate was added until pH 8 and the organic phase was separated. The aqueous phase was extracted with dichloromethane (2 ×20 ml) and the combined organic phases were washed with brine (10 ml), dried over magnesium sulfate and concentrated in vacuo to give 4.2 g of (2R)-N-((1R)-1-dimethylcarbamoyl-2- phenylethyl)-N-methyl-2-methylamino-3-(2-naphthyl) propionamide.

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with dichloromethane (2 ×20 ml)
  3. washthe combined organic phases were washed with brine (10 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76df851efebb421cbb64083ec98a7981
Source dataset
uspto-grants-1999_11
Patent number
US05977178

Reaction notes

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