Trifluoroacetic acid methylene chloride → HCID 118260143, compound

HRID 1779202Notes

Reaction equation

HRID 1779202 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:30]=[CH:31]/[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38](=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C@@:22]([OH:29])([CH2:26][CH2:27][OH:28])[C:23]([OH:25])=O)=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].ClCCl.FC(F)(F)C(O)=O>>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:18][C:19](=[O:20])[C@H:21]([C@@:22]2([OH:29])[CH2:26][CH2:27][O:28][C:23]2=[O:25])/[CH:30]=[CH:31]/[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38](=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 90060184HCID 90060184, compound

Product 1

HCID 118260143HCID 118260143, compoundYield 56%

Procedure

To No. 5214357, (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoic acid (20 mg, 0.0310 mmol) was added a mixture of dichloromethane/trifluoroacetic acid (9/1, v/v, 2 mL) and the mixture was stirred at room temperature for 1 hour. After confirming the consumption of the starting materials by LCMS, the organic solvent was distilled off under reduced pressure. The resulting residue was purified by preparative HPLC and then freeze-dried to obtain No. 5214805 (11 mg, 56% yield, white powder).

Workup

  1. customthe consumption of the starting materials by LCMS
  2. distillationthe organic solvent was distilled off under reduced pressure
  3. customThe resulting residue was purified by preparative HPLC
  4. customfreeze-dried
  5. customto obtain No

Sources & evidence

ORD record
ord-7ec06992ee984de1895df2d3389f4ee5
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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