Ammonium Chloride → HCID 67076976, compound

HRID 1348628Notes

Reaction equation

HRID 1348628 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C([N-]C(C)C)(C)C.[Li+].[CH:30]1([CH:33]=[O:34])[CH2:32][CH2:31]1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([N:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:33]([CH:30]1[CH2:32][CH2:31]1)[OH:34])[CH3:2]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 123114CyclopropanecarboxaldehydeHCID 2724682Lithium diisopropylamideHCID 3553452Ethyl 2-(dibenzylamino)acetate

Product 1

HCID 67076976HCID 67076976, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 44.2 g (156 mmol) dibenzylamino-acetic acid ethyl ester in 300 ml tetrahydrofuran was stirred at −70° C. with 92.0 ml (184 mmol) lithium diisopropylamide (2M in heptane) for 60 minutes. 14.0 ml (184 mmol) cyclopropanecarboxaldehyde were added and stirring was continued overnight. The mixture was allowed to warm to room temperature an poured on saturated aqueous ammonium chloride. Extraction with diethyether and chromatography on silicagel with diethyether/heptane 1/2 yielded as first eluting fraction 17.1 g (31%) racemic (2R,3S and 2S,3R)-3-cyclopropyl-2-dibenzylamino-3-hydroxy-propionic acid ethyl ester, MS m/e (%): 354.1 (M+H+, 100) and as second eluting fraction 20.1 g (36%) racemic (2R,3R and 2S,3S)-3-cyclopropyl-2-dibenzylamino-3-hydroxy-propionic acid ethyl ester, MS m/e (%): 354.3 (M+H+, 100).

Workup

  1. extractionExtraction with diethyether and chromatography on silicagel with diethyether/heptane 1/2

Sources & evidence

ORD record
ord-34f2e60c90e248faa1ae7be6f0db4364
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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