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

HRID 16927Notes

Reaction equation

HRID 16927 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-ad7603fc1a374a56b24c5d167c12ded6
Source dataset
uspto-grants-2010_06
Patent number
US07737266B2

Reaction notes

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