Ammonium Chloride → HCID 67076827, compound

HRID 1348666Notes

Reaction equation

HRID 1348666 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+].[CH2:30]([O:37][CH2:38][CH2:39][CH:40]=[O:41])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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:40]([OH:41])[CH2:39][CH2:38][O:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:2]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 3553452Ethyl 2-(dibenzylamino)acetateHCID 108882613-(Benzyloxy)propanal

Product 1

HCID 67076827HCID 67076827, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 42 g (148 mmol) dibenzylamino-acetic acid ethyl ester in 1 l tetrahydrofuran was stirred at −70° C. with 87 ml (77.6 mmol) lithium diisopropylamide (2M in tetrahydrofurane) for 60 minutes. 28.7 g (175 mmol) 3-(Benzyloxy)propanal were added and stirring was continued overnight. The mixture was allowed to warm to room temperature and 200 ml saturated aqueous ammonium chloride solution was added. Extraction with diethylether and chromatography on silicagel with ethylacetate/heptane 0:100 to 100:0 yielded as first eluting fraction 13.0 g (20%) racemic (2S,3R and 2R,3S)-5-benzyloxy-2-dibenzylamino-3-hydroxy-pentanoic acid ethyl ester, MS m/e (%): 448.1 (M+H+, 100) and as second diluting fraction 11.0 g (17%) racemic (2R,3R and 2S,3S)-5-benzyloxy-2-dibenzylamino-3-hydroxy-pentanoic acid ethyl ester, MS m/e (%): 448.1 (M+H+, 100).

Workup

  1. extractionExtraction with diethylether and chromatography on silicagel with ethylacetate/heptane 0:100 to 100:0

Sources & evidence

ORD record
ord-94a59cc4227d43449f28832c8efac8b8
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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