Diisopropylethylamine → benzyl (3S)-3-{[(benzyloxy)carbonyl]amino}-4-[(3,3-diethoxypropyl)amino]-4-oxobutanoate

HRID 25696

Reaction equation

HRID 25696 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:21]1[C:29]2N=NN[C:25]=2[CH:24]=[CH:23][CH:22]=1.Cl.[CH3:31]N(C)CCCN=C=NCC.[NH2:42][CH2:43][CH2:44][CH:45]([O:49][CH2:50][CH3:51])[O:46][CH2:47][CH3:48].C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:42][CH2:43][CH2:44][CH:45]([O:49][CH2:50][CH3:51])[O:46][CH2:47][CH3:48])=[O:19])[CH2:13][C:14]([O:16][CH2:31][C:21]1[CH:29]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723942N-(Benzyloxycarbonyl)aspartic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 59065876benzyl (3S)-3-{[(benzyloxy)carbonyl]amino}-4-[(3,3-diethoxypropyl)amino]-4-oxobutanoateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Reference Example 13, benzyloxycarbonyl-L-aspartic acid [1-benzyl ester (2 g, 5.6 mmol), hydroxybenzotriazole (756 mg, 5.6 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.07 g, 5.6 mmol), 1-amino-3,3-diethoxypropane (784 mg, 5.3 mmol) and N,N-diisopropylethylamine (0.986 mL, 5.6 mmol) were reacted in anhydrous tetrahydrofuran (30 ml) at room temperature for 16 hours, to provide benzyl (3S)-3-{[(benzyloxy)carbonyl]amino}-4-[(3,3-diethoxypropyl)amino]-4-oxobutanoate (2.81 g, 100%) as a pale yellow waxy solid.

Sources & evidence

ORD record
ord-d96b4e3070854d9da39bcc7490a10a3a
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Linked notes

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