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

HRID 1427742Notes

Reaction equation

HRID 1427742 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:41]=[CH:40][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][C:33]([O:35]C(C)(C)C)=[O:34])=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:41]=[CH:40][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1

Participants

3

Reactant 1

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

Product 1

HCID 904123311-((4-(4-(3-Aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oic acidYield 109.6%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate (3.24 g, 5.63 mmol) was dissolved in a solution of DCM:TFA (2:1, 20 ml) and stirred ca. 1 h. Upon completion, reaction was then concentrated under reduced pressure, co-evaporated with toluene, and dried on oil pump for 5 hs to yield 3.20 g of crude 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oic acid as yellow oil. The crude product was used without any further purification.

Workup

  1. customUpon completion, reaction
  2. concentrationwas then concentrated under reduced pressure, co-evaporated with toluene
  3. customdried on oil pump for 5 hs

Sources & evidence

ORD record
ord-f9f76e322ed0462c92d05029c5325c2c
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

Loading…