1,2-Dichloroethane → HCID 86295409, compound

HRID 1427741Notes

Reaction equation

HRID 1427741 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[CH2:9]([O:12][CH2:13][CH2:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:53]=[CH:52][C:25]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([NH:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][CH2:48][C:49](O)=[O:50])=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1)=[O:16])[C:10]#[CH:11].C(Cl)CCl>C(Cl)Cl>[CH2:9]([O:12][CH2:13][CH2:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:53]=[CH:52][C:25]([C:26]([C:28]2[CH:29]=[CH:30][C:31]([NH:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][CH2:48][C:49]([O:1][N:2]3[C:6](=[O:7])[CH2:5][CH2:4][C:3]3=[O:8])=[O:50])=[CH:32][CH:33]=2)=[O:27])=[CH:24][CH:23]=1)=[O:16])[C:10]#[CH:11]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 90411544HCID 90411544, compound

Product 1

HCID 86295409HCID 86295409, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-hydroxysuccinimide (252 mg, 2.30 mmol) was added to a solution of 1-((4-(4-(3-(3-(prop-2-yn-1-yloxy)propanamido)propoxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oic acid (1.25 g, 1.98 mmol) in anhydrous DCM (10 ml) was added followed by EDC (505 mg, 2.64 mmol). The reaction was stirred at r.t. for 2-3 hs. Upon completion, reaction was concentrated under reduced pressure and purified by silica gel chromatography (DCM to DCM:iPrOH gradient) to provide 1.16 g (1.63 mmol, 80% yield) of 2,5-dioxopyrrolidin-1-yl 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. additionwas added
  2. customUpon completion, reaction
  3. concentrationwas concentrated under reduced pressure
  4. custompurified by silica gel chromatography (DCM to DCM:iPrOH gradient)

Sources & evidence

ORD record
ord-c366ebc24e844220a3fbf38db7e40e0e
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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