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

HRID 1027363Notes

Reaction equation

HRID 1027363 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 under vacuum, water was added to the residue, and the product was extracted with ethyl acetate. The crude product was purified by conversion into its hydrochloride salt.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum, water
  2. additionwas added to the residue
  3. extractionthe product was extracted with ethyl acetate
  4. customThe crude product was purified by conversion into its hydrochloride salt

Sources & evidence

ORD record
ord-19677dbb4d5049a3a06e9eb814b46d09
Source dataset
uspto-grants-2014_05
Patent number
US08735369B2

Reaction notes

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