L-Glutamic acid, N-((phenylmethoxy)carbonyl)- → HCID 59065896, compound

HRID 25698Notes

Reaction equation

HRID 25698 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([OH:20])=O)[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:22]1[C:30]2N=NN[C:26]=2C=CC=1.Cl.[CH3:32]N(C)CCCN=C=NCC.[NH2:43][CH2:44][CH2:45][CH:46]([O:50][CH2:51][CH3:52])[O:47][CH2:48][CH3:49].C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([NH:43][CH2:44][CH2:45][CH:46]([O:50][CH2:51][CH3:52])[O:47][CH2:48][CH3:49])=[O:20])[CH2:13][CH2:14][C:15]([O:17][C:30]([CH3:26])([CH3:22])[CH3:32])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 70866L-Glutamic acid, N-((phenylmethoxy)carbonyl)-HCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 59065896HCID 59065896, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Reference Example 13, benzyloxycarbonyl-L-glutamic acid □-t-butyl ester (2 g, 5.93 mmol), hydroxybenzotriazole (801 mg, 5.93 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.14 g, 5.93 mmol), 1-amino-3,3-diethoxypropane (830 mg, 5.65 mmol), and N,N-diisopropylethylamine (1.03 mL, 5.93 mmol) were reacted in anhydrous tetrahydrofuran (30 mL) at room temperature for 16 hours, to provide tert-butyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-[(3,3-diethoxypropyl)amino]-5-oxopentanoate (2.92 g, 100%) as a yellow waxy solid.

Sources & evidence

ORD record
ord-0fcb2e5ea0584bfd82f00c17a2df56d9
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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