1,2-Dichloroethane → Tert-butyl 1-((4-(4-(3-(3-(prop-2-yn-1-yloxy)propanamido)propoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate

HRID 1427740Notes

Reaction equation

HRID 1427740 reaction equation
C(Cl)CCl.[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:45]=[CH:44][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:18][CH:17]=2)=[O:15])=[CH:12][CH:11]=1.[CH2:46]([O:49][CH2:50][CH2:51][C:52](O)=[O:53])[C:47]#[CH:48].ON1C(=O)CCC1=O>C(Cl)Cl>[CH2:46]([O:49][CH2:50][CH2:51][C:52]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:45]=[CH:44][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])=[CH:18][CH:17]=2)=[O:15])=[CH:12][CH:11]=1)=[O:53])[C:47]#[CH:48]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 2879343-(Prop-2-yn-1-yloxy)propanoic acidHCID 90411873Tert-butyl 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate

Product 1

HCID 90412025Tert-butyl 1-((4-(4-(3-(3-(prop-2-yn-1-yloxy)propanamido)propoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oateYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDC (0.77 g, 4.00 mmol) was added to a solution of tert-butyl 1-((4-(4-(3-aminopropoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate (2.00 g, 3.48 mmol), 3-(prop-2-yn-1-yloxy)propanoic acid (0.45 g, 3.48 mmol) and N-hydroxysuccinimide (0.06 g, 0.52 mmol) in DCM (12 mL) at r.t. and the reaction mixture was stirred for 4 hs at room temperature. Upon completion, reaction was concentrated under reduced pressure and purified by silica gel chromatography (EtOAc toEtOAc:MeOH, gradient) to provide 2.12 g (3.10 mmol, 89% yield) of tert-butyl 1-((4-(4-(3-(3-(prop-2-yn-1-yloxy)propanamido)propoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oate as slightly yellow oil.

Workup

  1. customUpon completion, reaction
  2. concentrationwas concentrated under reduced pressure
  3. custompurified by silica gel chromatography (EtOAc toEtOAc:MeOH, gradient)

Sources & evidence

ORD record
ord-6c9048e71449401c999085b9cc486cb7
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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