tert-butyl (3-(2-(2-(3-((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)propoxy)ethoxy)ethoxy)propyl)carbamate → N-(3-(4-(4-((3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)amino)-benzoyl)phenoxy)propyl)-1-(5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)-3,6,9,12-tetraoxapentadecan-15-amide

HRID 1427735Notes

Reaction equation

HRID 1427735 reaction equation
[O:1]=[C:2]([CH2:44][CH2:45][O:46][CH2:47][CH2:48][O:49][CH2:50][CH2:51][O:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][NH:58][C:59](=[O:73])[CH2:60][CH2:61][CH2:62][CH2:63][CH:64]1[CH:71]2[CH:67]([NH:68][C:69](=[O:72])[NH:70]2)[CH2:66][S:65]1)[NH:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:43]=[CH:42][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][NH:34]C(=O)OC(C)(C)C)=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:34][CH2:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][CH2:21][NH:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]([C:11]2[CH:42]=[CH:43][C:8]([O:7][CH2:6][CH2:5][CH2:4][NH:3][C:2](=[O:1])[CH2:44][CH2:45][O:46][CH2:47][CH2:48][O:49][CH2:50][CH2:51][O:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][NH:58][C:59](=[O:73])[CH2:60][CH2:61][CH2:62][CH2:63][CH:64]3[CH:71]4[CH:67]([NH:68][C:69](=[O:72])[NH:70]4)[CH2:66][S:65]3)=[CH:9][CH:10]=2)=[O:13])=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 90442026tert-butyl (3-(2-(2-(3-((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)propoxy)ethoxy)ethoxy)propyl)carbamate

Product 1

HCID 90411535N-(3-(4-(4-((3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)amino)-benzoyl)phenoxy)propyl)-1-(5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)-3,6,9,12-tetraoxapentadecan-15-amideYield 98%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl (3-(2-(2-(3-((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)propoxy)ethoxy)ethoxy)propyl)carbamate (16.1 g, 15.92 mmol) was dissolved in a solution of DCM:TFA (2:1, 96 ml) and the reaction mixture was stirred for ca. 1 h at r.t. Upon completion, reaction was then concentrated under reduced pressure, co-evaporated with toluene, and dried on pump for 5 hs to yield 14.13 g (98% yield) of crude N-(3-(4-(4-((3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)amino)benzoyl)phenoxy)propyl)-1-(5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)-3,6,9,12-tetraoxapentadecan-15-amide as yellow oil.

Workup

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

Sources & evidence

ORD record
ord-7bb94ce913a6443d8e2334cdc7c7d921
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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