3-{Ethoxycarbonylmethyl-[6-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoyl]-amino)-propionic acid ethyl ester → 3-[(6-Amino-hexanoyl)-ethoxycarbonylmethyl-amino]-propionic acid ethyl ester

HRID 20890Notes

Reaction equation

HRID 20890 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH2:6][N:7]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:8](=[O:32])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[CH3:2]>N1CCCCC1.CN(C)C=O>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH2:6][N:7]([C:8](=[O:32])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH3:2]

Participants

4

Reactant 1

HCID 596438903-{Ethoxycarbonylmethyl-[6-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoyl]-amino)-propionic acid ethyl ester

Product 1

HCID 596438883-[(6-Amino-hexanoyl)-ethoxycarbonylmethyl-amino]-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8082PiperidineSolvent

Procedure

3-{Ethoxycarbonylmethyl-[6-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoyl]-amino}-propionic acid ethyl ester AB (11.5 g, 21.3 mmol) was dissolved in 20% piperidine in dimethylformamide at 0° C. The solution was continued stirring for 1 h. The reaction mixture was concentrated in vacuum and the residue water was added and the product was extracted with ethyl acetate. The crude product was purified by converting into hydrochloride salt.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum
  2. additionthe residue water was added
  3. extractionthe product was extracted with ethyl acetate
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-ff07496bf4054a7eaff388a58049f106
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Reaction notes

Loading…