Pyridine → 2,2,2-trichloroethyl 10-[5-(Boc-amino)-4-oxopentanoyloxy]decanoate

HRID 1771053Notes

Reaction equation

HRID 1771053 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][C:27]([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28].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][C:27]([O:29][CH2:30][C:31]([Cl:32])([Cl:33])[Cl:34])=[O:28])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 106634502,2,2-Trichloroethyl 10-hydroxydecanoateHCID 179898205-((tert-Butoxycarbonyl)amino)-4-oxopentanoic acid

Product 1

HCID 900345582,2,2-trichloroethyl 10-[5-(Boc-amino)-4-oxopentanoyloxy]decanoateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from 5-(Boc-amino)-4-oxopentanoic acid (1.00 g; 4.3 mmol), the product from 12a (1.37 g; 4.3 mmol), N,N′-dicyclohexylcarbodiimide (DCC, 1.03 g; 5.0 mmol), and pyridine (2.0 mL) in dichloromethane (40 mL) using Procedure E. The crude product was purified on a 100×50 mm silica gel 60 column eluted with ethyl acetate-hexane (1:2), collecting 16×50 mL fractions. From evaporation of fractions 4-9 gave 1.6 g (71%) product was obtained (yellowish oil).

Workup

  1. customThe crude product was purified on a 100×50 mm silica gel 60 column
  2. washeluted with ethyl acetate-hexane (1:2)
  3. customcollecting 16×50 mL fractions
  4. customFrom evaporation of fractions 4-9

Sources & evidence

ORD record
ord-7941edeb037e4a96b5dd4232491ec8e2
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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