Pyridine → 2,2,2-trichloroethyl 12-[5-(Boc-amino)-4-oxopentanoyloxy]dodecanoate

HRID 1771059Notes

Reaction equation

HRID 1771059 reaction equation
[C:1]([NH:8][CH2:9][C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][C:33]([Cl:36])([Cl:35])[Cl:34])=[O:30].C1(N=C=NC2CCCCC2)CCCCC1.N1C=CC=CC=1>ClCCl>[C:1]([NH:8][CH2:9][C:10](=[O:16])[CH2:11][CH2:12][C:13]([O:15][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][C:33]([Cl:34])([Cl:35])[Cl:36])=[O:30])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 179898205-((tert-Butoxycarbonyl)amino)-4-oxopentanoic acidHCID 900345192,2,2-Trichloroethyl 12-hydroxydodecanoate

Product 1

HCID 1182071072,2,2-trichloroethyl 12-[5-(Boc-amino)-4-oxopentanoyloxy]dodecanoateYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from 5-(Boc-amino)-4-oxopentanoic acid (2.0 g; 8.6 mmol), the product of 14a (3.0 g; 8.6 mmol), N,N′-dicyclohexylcarbodiimide (DCC, 2.1 g; 10.0 mmol), and pyridine (4.0 mL) in dichloromethane (75 mL) using Procedure E. The crude product was purified on a 90×50 mm silica gel 60 column eluted with ethyl acetate-hexane (1:3), collecting 13×50 mL fractions. Following evaporation of fractions 6-11, 1.44 g (30%) product was obtained (yellowish oil).

Workup

  1. customThe crude product was purified on a 90×50 mm silica gel 60 column
  2. washeluted with ethyl acetate-hexane (1:3)
  3. customcollecting 13×50 mL fractions
  4. customevaporation of fractions 6-11

Sources & evidence

ORD record
ord-d2bc29f2427d4ee2ab96fa7eab680450
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

Loading…