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3-Aminophenol → tert-Butyl (2-(7-((3-hydroxyphenyl)amino)-7-oxoheptanamido)phenyl)carbamate

HRID 2276702
Notes
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Reaction equation

HRID 2276702 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:26][C:27]1[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[OH:33][C:29]1[CH:28]=[C:27]([NH:26][C:22](=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:16]([NH:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:25])[CH:32]=[CH:31][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 115683-AminophenolHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 95435387-((2-((Tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-((2-((tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoic acid (1.0 g, 2.85 mmol) in DMF (20 mL) was added 3-aminophenol (0.31 g, 2.85 mmol), HBTU (1.1 g, 2.85 mmol), DIEA (2 mL, 11.4 mmol). The mixture was stirred at room temperature for 12 hours. The resulting mixture was poured into water and extracted by EtOAc (100 mL×3). The organic layers were combined and washed with saturated aqueous solution of Na2CO3, dried over Na2SO4 and then the resulting solution was used directly for next step without further purification.

Workup

  1. extractionextracted by EtOAc (100 mL×3)
  2. washwashed with saturated aqueous solution of Na2CO3
  3. dry with materialdried over Na2SO4
  4. customthe resulting solution was used directly for next step without further purification

Sources & evidence

ORD record
ord-47b6c57e1d734f29934cd9b2b7832096
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133105B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes