1,2-Dichloroethane → HCID 90412413, compound

HRID 1427745Notes

Reaction equation

HRID 1427745 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[O:9]=[C:10]1[CH:14]=[CH:13][C:12](=[O:15])[N:11]1[CH2:16][CH2:17][C:18](=[O:73])[NH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][C:34](=[O:72])[NH:35][CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:71]=[CH:70][C:43]([C:44]([C:46]2[CH:51]=[CH:50][C:49]([NH:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH2:62][CH2:63][O:64][CH2:65][CH2:66][C:67](O)=[O:68])=[CH:48][CH:47]=2)=[O:45])=[CH:42][CH:41]=1.C(Cl)CCl>C(Cl)Cl>[O:9]=[C:10]1[CH:14]=[CH:13][C:12](=[O:15])[N:11]1[CH2:16][CH2:17][C:18](=[O:73])[NH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][C:34](=[O:72])[NH:35][CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:41]=[CH:42][C:43]([C:44]([C:46]2[CH:51]=[CH:50][C:49]([NH:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH2:62][CH2:63][O:64][CH2:65][CH2:66][C:67]([O:1][N:2]3[C:6](=[O:7])[CH2:5][CH2:4][C:3]3=[O:8])=[O:68])=[CH:48][CH:47]=2)=[O:45])=[CH:70][CH:71]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 90412089HCID 90412089, compound

Product 1

HCID 90412413HCID 90412413, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-hydroxysuccinimide (438 mg, 4.00 mmol) was added to a solution of crude 1-((4-(4-((1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,19-dioxo-7,10,13,16-tetraoxa-4,20-diazatricosan-23-yl)oxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oic acid (3.00 g) in anhydrous DCM (20 ml) was added followed by EDC (946 mg, 5.00 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 2.15 g (2.12 mmol) of 2,5-dioxopyrrolidin-1-yl 1-((4-(4-((1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,19-dioxo-7,10,13,16-tetraoxa-4,20-diazatricosan-23-yl)oxy)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-67f7e052b0004334be9a68fbce56e41a
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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