1,2-Dichloroethane → HCID 86295410, compound

HRID 1427738Notes

Reaction equation

HRID 1427738 reaction equation
[O:1]=[C:2]([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][NH:54][C:55](=[O:69])[CH2:56][CH2:57][CH2:58][CH2:59][CH:60]1[CH:67]2[CH:63]([NH:64][C:65](=[O:68])[NH:66]2)[CH2:62][S:61]1)[NH:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:39]=[CH:38][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1.O[N:71]1[C:75](=[O:76])[CH2:74][CH2:73][C:72]1=[O:77].C(Cl)CCl>C(Cl)Cl>[O:1]=[C:2]([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][NH:54][C:55](=[O:69])[CH2:56][CH2:57][CH2:58][CH2:59][CH:60]1[CH:67]2[CH:63]([NH:64][C:65](=[O:68])[NH:66]2)[CH2:62][S:61]1)[NH:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:39]=[CH:38][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][C:35]([O:37][N:71]3[C:75](=[O:76])[CH2:74][CH2:73][C:72]3=[O:77])=[O:36])=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 90412086HCID 90412086, compound

Product 1

HCID 86295410HCID 86295410, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 1-((4-(4-((5,21-dioxo-25-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-8,11,14,17-tetraoxa-4,20-diazapentacosyl)oxy)benzoyl)phenyl)amino)-3,6,9,12-tetraoxapentadecan-15-oic acid (1.85 g, 1.89 mmol) in anhydrous DCM (43.0 ml) was added N-hydroxysuccinimide (239 mg, 2.08 mmol) followed by EDC (471 mg, 2.46 mmol). The reaction was stirred at r.t. for 4 hs. Upon completion, reaction was concentrated under reduced pressure and purified by silica gel chromatography (DCM to DCM:iPrOH, gradient) to provide 2,5-dioxopyrrolidin-1-yl 1-((4-(4-((5,21-dioxo-25-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-8,11,14,17-tetraoxa-4,20-diazapentacosyl)oxy)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 (DCM to DCM:iPrOH, gradient)

Sources & evidence

ORD record
ord-7904b8b303d040c697700c2067d826ca
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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