Sodium Carbonate → N-[4-ethoxycarbonyl-(S,S)-2,4-di-benzylbutyryl]-O-benzyl-(L)-serine

HRID 374314Notes

Reaction equation

HRID 374314 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:21]([O:23][C:24]([C@H:26]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:27][C@@H:28]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:29](Cl)=[O:30])=[O:25])[CH3:22]>O>[CH2:21]([O:23][C:24]([C@H:26]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:27][C@@H:28]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:29]([NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:30])=[O:25])[CH3:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 78457O-benzyl-L-serineHCID 149971304-ethoxycarbonyl-(S,S)-2,4-dibenzylbutyryl chloride

Product 1

HCID 14997131N-[4-ethoxycarbonyl-(S,S)-2,4-di-benzylbutyryl]-O-benzyl-(L)-serine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.3 g of O-benzyl-(S)-serine and 1.8 g of sodium carbonate in 30 ml of water at 0° is added to 2.2 g of 4-ethoxycarbonyl-(S,S)-2,4-dibenzylbutyryl chloride and the mixture is stirred at room temperature for 4 hours. The mixture is extracted with ether, and the aqueous layer is acidified with 2N hydrochloric acid. The acidic solution is extracted with ethyl acetate, washed with saturated brine, dried (magnesium sulfate), filtered and concentrated to yield N-[4-ethoxycarbonyl-(S,S)-2,4-di-benzylbutyryl]-O-benzyl-(L)-serine.

Workup

  1. extractionThe mixture is extracted with ether
  2. extractionThe acidic solution is extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-21cdc161b6b24cbbb65e6134b73769c9
Source dataset
uspto-grants-1992_11
Patent number
US05166212

Reaction notes

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