Water → Tert-butyl 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate

HRID 1427737Notes

Reaction equation

HRID 1427737 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:62]=[CH:61][C:30]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([NH:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])=[CH:35][CH:34]=2)=[O:32])=[CH:29][CH:28]=1)=[N+]=[N-].O>CCOCC.C1COCC1>[NH2:20][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:62]=[CH:61][C:30]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([NH:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][C:54]([O:56][C:57]([CH3:58])([CH3:60])[CH3:59])=[O:55])=[CH:35][CH:34]=2)=[O:32])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 90413692Tert-butyl 1-((4-(4-(3-azidopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate

Product 1

HCID 90411873Tert-butyl 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oateYield 68.7%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

Triphenylphosphine (2.62 g, 10.0 mmol) was added to a solution of tert-butyl 1-((4-(4-(3-azidopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate (5.0 g 8.32 mmol) in Ether:THF (1:1, 50 mL) at 0° C. followed by of water (500 mg, 27.8 mmol). The reaction was stirred at r.t. overnight. Upon completion, the reaction was concentrated and purified by silica gel chromatography (EtOAc to EtOAc:MeOH gradient with 1% TEA) to provide 3.24 g (5.63 mmo 68.7% yield) of tert-butyl 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate as yellow oil.

Workup

  1. concentrationUpon completion, the reaction was concentrated
  2. custompurified by silica gel chromatography (EtOAc to EtOAc:MeOH gradient with 1% TEA)

Sources & evidence

ORD record
ord-fcd6df3c61454f6c9a99d6c266836174
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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