Triethylamine → HCID 86723934, compound

HRID 1475292Notes

Reaction equation

HRID 1475292 reaction equation
[C:1]([O:8]C([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.[CH2:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13].[CH2:19]([C@H:21]1[CH2:26][NH:25][C@H:24]([CH3:27])[CH2:23][N:22]1[CH2:28][C:29]([OH:31])=[O:30])[CH3:20]>C(Cl)Cl>[CH2:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13].[C:4]([O:3][C:1]([N:25]1[CH2:26][C@H:21]([CH2:19][CH3:20])[N:22]([CH2:28][C:29]([OH:31])=[O:30])[CH2:23][C@H:24]1[CH3:27])=[O:8])([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22064466Tert-butyldicarbonateHCID 86723933HCID 86723933, compound

Product 1

HCID 86723934HCID 86723934, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl dicarbonate (2.1 g, 9.6 mmol) and triethylamine (6.7 mL, 48.4 mmol) were added to a suspension of ((2S,5R)-2-ethyl-5-methyl-piperazin-1-yl)-acetic acid (1.8 g, 9.6 mmol) in DCM. The resulting solution was stirred at room temperature for 24 h. The solvent was removed in vacuo to give (2R,5S)-4-carboxymethyl-5-ethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester triethylamine salt (3.8 g) as a yellow gum. 1H NMR (CDCl3): 11.73-9.75 (1H, m), 4.20 (1H, s), 3.86 (1H, d), 3.34-3.07 (3H, m), 2.97 (6H, q, triethylamine), 2.77-2.65 (2H, m), 2.60 (1H, dd), 1.47-1.36 (11H, m), 1.26 (3H, d), 1.24-1.14 (9H, m, triethylamine), 0.87 (3H, t).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d85f0294f2a7413a9e62dab347c81e66
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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