Trifluoroacetic acid → (S)-16-(3-((4-cyclobutoxy-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)phenyl)-4,7,10,13-tetraoxahexadecan-1-oic acid

HRID 625504Notes

Reaction equation

HRID 625504 reaction equation
[CH:1]1([O:5][C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]3[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[CH:18]=[CH:19][CH:20]=3)=[O:14])=[C:8]([C:43]3[CH:48]=[C:47]([C:49](=[O:61])[NH:50][C@@H:51]4[C:60]5[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=5)[CH2:54][CH2:53][CH2:52]4)[CH:46]=[CH:45][N:44]=3)[CH:7]=2)[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>>[CH:1]1([O:5][C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]3[CH:16]=[C:17]([CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])[CH:18]=[CH:19][CH:20]=3)=[O:14])=[C:8]([C:43]3[CH:48]=[C:47]([C:49](=[O:61])[NH:50][C@@H:51]4[C:60]5[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=5)[CH2:54][CH2:53][CH2:52]4)[CH:46]=[CH:45][N:44]=3)[CH:7]=2)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66586867(S)-tert-butyl 16-(3-((4-cyclobutoxy-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)phenyl)-4,7,10,13-tetraoxahexadecan-1-oate

Product 1

HCID 89946299(S)-16-(3-((4-cyclobutoxy-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)phenyl)-4,7,10,13-tetraoxahexadecan-1-oic acidYield 64%

Procedure

To (S)-tert-butyl 16-(3-((4-cyclobutoxy-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)phenyl)-4,7,10,13-tetraoxahexadecan-1-oate Example 284 was added trifluoracetic acid (1 mL). The mixture was stirred for 5 minutes, concentrated and purified by prep. TLC to give a yellow syrup (7.2 mg, 64%). MS (ES, m/z): 780.5[M+H]+.

Workup

  1. concentrationconcentrated
  2. custompurified by prep

Sources & evidence

ORD record
ord-b06433f1c3e9479d92d7df952740fe7d
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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