Trifluoroacetic acid → HCID 117710436, compound

HRID 339260Notes

Reaction equation

HRID 339260 reaction equation
[C:1]([OH:7])([C:3](F)(F)F)=[O:2].[CH3:8][C:9]([CH3:79])([CH3:78])[C@H:10]([NH:71][C:72](=[O:77])[C@@H:73]([NH:75][CH3:76])[CH3:74])[C:11]([N:13]1[C@H:17]([C:18](=[O:30])[NH:19][C@H:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22][CH2:21]2)[CH2:16][C@H:15]([C:31]2[CH:40]=[C:39]3[C:34]([CH2:35][C@@H:36]([C:58]([NH:60][C@H:61]4[C:70]5[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=5)[CH2:64][CH2:63][CH2:62]4)=[O:59])[N:37]([C:41](=[O:57])[C@@H:42]([NH:50][C:51](=[O:56])[C@@H:52]([NH:54][CH3:55])[CH3:53])[C:43]([S:46]CCO)([CH3:45])[CH3:44])[CH2:38]3)=[CH:33][CH:32]=2)[CH2:14]1)=[O:12]>>[CH3:79][C:9]([CH3:8])([CH3:78])[C@H:10]([NH:71][C:72](=[O:77])[C@@H:73]([NH:75][CH3:76])[CH3:74])[C:11]([N:13]1[C@H:17]([C:18](=[O:30])[NH:19][C@H:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22][CH2:21]2)[CH2:16][C@H:15]([C:31]2[CH:40]=[C:39]3[C:34]([CH2:35][C@@H:36]([C:58](=[O:59])[NH:60][C@H:61]4[C:70]5[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=5)[CH2:64][CH2:63][CH2:62]4)[N:37]([C:41](=[O:57])[C@@H:42]([NH:50][C:51](=[O:56])[C@@H:52]([NH:54][CH3:55])[CH3:53])[C:43]([S:46][CH2:3][C:1]([OH:7])=[O:2])([CH3:44])[CH3:45])[CH2:38]3)=[CH:33][CH:32]=2)[CH2:14]1)=[O:12]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117710492HCID 117710492, compound

Product 1

HCID 117710436HCID 117710436, compoundYield 22.3%

Procedure

A solution of TFA (20% in CH2Cl2, 1.06 mmol) was added to Compound F of Example 28 (13 mg, 0.011 mmol). The resulting reaction mixture was stirred at room temperature for 1 h and then concentrated in vacuo. The crude oil was purified by preparative HPLC to give the title compound (2.5 mg, 18%) as a white solid after lyophilization. MS (ESI+) m/z 1021.6 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. customThe crude oil was purified by preparative HPLC

Sources & evidence

ORD record
ord-7dcb6b282bf14ec79d1133cc5db6ade8
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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