Diisopropylethylamine → benzyl (1S)-2-[(3,3-diethoxypropyl)amino]-1-methyl-2-oxoethylcarbamate

HRID 25692

Reaction equation

HRID 25692 reaction equation
[C:1]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[NH2:39][CH2:40][CH2:41][CH:42]([O:46][CH2:47][CH3:48])[O:43][CH2:44][CH3:45].C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:44]([O:43][CH:42]([O:46][CH2:47][CH3:48])[CH2:41][CH2:40][NH:39][C:14](=[O:16])[C@@H:12]([NH:11][C:1](=[O:2])[O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH3:13])[CH3:45]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 736104N-carbobenzyloxyalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 59065857benzyl (1S)-2-[(3,3-diethoxypropyl)amino]-1-methyl-2-oxoethylcarbamateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Reference Example 13, carbobenzyloxy-L-alanine (2 g, 8.99 mmol), hydroxybenzotriazole (1.2 g, 8.99 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.72 g, 8.99 mmol), 1-amino-3,3-diethoxypropane (1.25 g, 8.53 mmol) and N,N-diisopropylethylamine (1.56 ml, 8.99 mmol) were reacted in anhydrous tetrahydrofuran (40 ml) at room temperature for 16 h, to provide benzyl (1S)-2-[(3,3-diethoxypropyl)amino]-1-methyl-2-oxoethylcarbamate (2.55 g, 85%) as a pale yellow solid.

Sources & evidence

ORD record
ord-4c22e671e5fc4c8db74fcd3b242ad080
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Linked notes

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