Triethylamine → Glycine methyl ester N-(butoxycarbonyl)pipecolinamide

HRID 1489534Notes

Reaction equation

HRID 1489534 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>>[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

5

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

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 crystalline solid: mp 118.5°-119.5° C. (EtOAc/isooctane 1:3); 1H-NMR (CDCl3) σ 6.60 (br s, 1H, CONH), 4.81 (m, 1H), 3.82-4.35 (complex m, 4H), 3.76 (s, 3H, OMe), 2.89 (m, 1H), 2.32 (m, 1H), 1.33-1.72 (complex m, 4H), 1.49 (s, 9H, tBu); Anal (calcd for C14H24 N2O5): C 55.99, H 8.05, N 9.33. Found: C 56.00, H 8.09, N 9.36.

Sources & evidence

ORD record
ord-560649217cfe4663b2aa9d296d326581
Source dataset
uspto-grants-1997_10
Patent number
US05679679

Reaction notes

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