tert-Butyl (2-(7-((3-hydroxyphenyl)amino)-7-oxoheptanamido)phenyl)carbamate → N1-(2-aminophenyl)-N7-(3-hydroxyphenyl)heptanediamide

HRID 2276703Notes

Reaction equation

HRID 2276703 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:32])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH:24]C(=O)OC(C)(C)C)=[O:16])[CH:5]=[CH:6][CH:7]=1>CCOC(C)=O>[NH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1)=[O:32]

Participants

3

Reactant 1

HCID 90399145tert-Butyl (2-(7-((3-hydroxyphenyl)amino)-7-oxoheptanamido)phenyl)carbamate

Product 1

HCID 78319017N1-(2-aminophenyl)-N7-(3-hydroxyphenyl)heptanediamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The solution of tert-Butyl (2-(7-((3-hydroxyphenyl)amino)-7-oxoheptanamido)phenyl)carbamate in EtOAc was stirred at 0° C. and bubbled with HCl gas for 20 min. The pH value of the solution was adjusted to 6 by saturated aqueous solution of Na2CO3. The aqueous phase was extracted with EtOAc (100 mL). The organic layers were combined and dried over Na2SO4 and then concentrated to give the crude product. The crude product was purified by flash chromatography SiO2 (EtOAc) to give desired compound CC No. 2 (0.25 g, yield 25.7%).

Workup

  1. custombubbled with HCl gas for 20 min
  2. extractionThe aqueous phase was extracted with EtOAc (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThe crude product was purified by flash chromatography SiO2 (EtOAc)

Sources & evidence

ORD record
ord-fd5e55548a6649419d9e01ced4e1de7f
Source dataset
uspto-grants-2015_09
Patent number
US09133105B2

Reaction notes

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