Dicyclohexylcarbodiimide → HCID 14850762, compound

HRID 345327Notes

Reaction equation

HRID 345327 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][C@@H:10]([CH2:12][P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2].[C:21]([O:25][C:26]([NH:28][CH2:29][C:30](O)=[O:31])=[O:27])([CH3:24])([CH3:23])[CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][C@@H:10]([CH2:12][P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8][N:7]1[C:30](=[O:31])[CH2:29][NH:28][C:26]([O:25][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:27])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 14850759HCID 14850759, compound

Product 1

HCID 14850762HCID 14850762, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g of cis 4-diethylphosphonomethyl-2-piperidinecarboxylic acid ethyl ester is reacted with 552 mg of N-t-butoxycarbonylglycine in the presence of N,N'-dicyclohexyl-carbodiimide in 10 ml of methylene chloride of room temperature for 16 hours to yield cis 1-[alpha-(t-butoxycarbonylamino)acetyl]-4-diethylphosphonomethyl-2-piperidinecarboxylic acid ethyl ester as an oil. Treatment with trimethylsilyl iodide yields cis 1-(alpha-aminoacetyl)-4-phosphonomethyl-2-piperidine

Sources & evidence

ORD record
ord-c7f19f635b4b43d4953834ac215b1c26
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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