Triethylamine → Glycine methyl ester N-(butoxycarbonyl)pipecolinamide

HRID 382268Notes

Reaction equation

HRID 382268 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=O)(C)(C)C.Cl.[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH2:22].Cl.CN([CH2:28][CH2:29][CH2:30]N=C=NCC)C.CC[N:38](CC)CC>CCOC(C)=O.C(CC(C)(C)C)(C)C>[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH2:22].[CH2:18]([O:19][C:20]([NH:38][C:14](=[O:16])[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]1)=[O:23])[CH2:30][CH2:29][CH3:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 70024518Glycine methyl ester N-(butoxycarbonyl)pipecolinamide

Reagents, catalysts & solvents 1

HCID 18516502EtOAc isooctaneSolvent

Procedure

1-(tertButoxycarbonyl)-2-piperidinecarboxylic acid (11.46 g, 1.2 eq), glycine methyl ester hydrochloride (9.42 g), 1-(dimethylaminopropyl)-3-(ethyl)carbodiimide hydrochloride (8.00 g, 1.0 eq) and Et3N (16.3 mL) were reacted as described in Example 1 to give 5.6 g of the title compound as a colorless crystallinesolid: mp 118.5-119.5° C. (EtOAc/isooctane 1:3);

Sources & evidence

ORD record
ord-6ab6b134d9d349a0a67fd8918d56b30c
Source dataset
uspto-grants-2001_10
Patent number
US06310064B1

Reaction notes

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