HCID 90412407, compound → HCID 90412089, compound

HRID 1427744Notes

Reaction equation

HRID 1427744 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][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][C:59]([O:61]C(C)(C)C)=[O:60])=[CH:40][CH:39]=2)=[O:37])=[CH:34][CH:33]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[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:33]=[CH:34][C:35]([C:36]([C:38]2[CH:43]=[CH:42][C:41]([NH:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][C:59]([OH:61])=[O:60])=[CH:40][CH:39]=2)=[O:37])=[CH:66][CH:67]=1

Participants

3

Reactant 1

HCID 90412407HCID 90412407, compound

Product 1

HCID 90412089HCID 90412089, compoundYield 116%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl 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 (7.36 g, 7.85 mmol) was dissolved in a solution of DCM:TFA (2:1, 50 ml) and left to stir for ca. 1 h. Upon completion, reaction was then concentrated under reduced pressure, co-evaporated with toluene, and dried on oil pump overnight to yield 8.35 g 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 as yellow oil.

Workup

  1. waitleft
  2. customUpon completion, reaction
  3. concentrationwas then concentrated under reduced pressure, co-evaporated with toluene
  4. customdried on oil
  5. waitpump overnight

Sources & evidence

ORD record
ord-709ef1bdb0be4b3cb87e0b0d728108b5
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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