HCID 90442027, compound → HCID 90412436, compound

HRID 1427743Notes

Reaction equation

HRID 1427743 reaction equation
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][C:10](=[O:69])[NH:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26](=[O:68])[NH:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:67]=[CH:66][C:35]([C:36]([C:38]2[CH:43]=[CH:42][C:41]([NH:44][CH2:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][CH2:57][NH:58]C(=O)OC(C)(C)C)=[CH:40][CH:39]=2)=[O:37])=[CH:34][CH:33]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:58][CH2:57][CH2:56][CH2:55][O:54][CH2:53][CH2:52][O:51][CH2:50][CH2:49][O:48][CH2:47][CH2:46][CH2:45][NH:44][C:41]1[CH:40]=[CH:39][C:38]([C:36]([C:35]2[CH:66]=[CH:67][C:32]([O:31][CH2:30][CH2:29][CH2:28][NH:27][C:26](=[O:68])[CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][NH:11][C:10](=[O:69])[CH2:9][CH2:8][N:3]3[C:4](=[O:7])[CH:5]=[CH:6][C:2]3=[O:1])=[CH:33][CH:34]=2)=[O:37])=[CH:43][CH:42]=1

Participants

3

Reactant 1

HCID 90442027HCID 90442027, compound

Product 1

HCID 90412436HCID 90412436, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl (3-(2-(2-(3-((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)propoxy)ethoxy)ethoxy)propyl)carbamate (6.31 g, 6.50 mmol) was dissolved in a solution of DCM:TFA (2:1, 60 ml) and stirred ca. 1 h. Upon completion, reaction was then concentrated under reduced pressure, co-evaporated with toluene, and dried on oil pump for 2 hs to yield 6.15 g of crude N-(3-(4-(4-((3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)-amino)benzoyl)phenoxy)propyl)-1-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido)-3,6,9,12-tetraoxapentadecan-15-amide as yellow oil. The crude product was used without any further purification.

Workup

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

Sources & evidence

ORD record
ord-a8eb58324d75477980089bfdfc1edf64
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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