Water → HCID 118260146, compound

HRID 1779209Notes

Reaction equation

HRID 1779209 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:16][C:17]([C@@H:19](/[CH:32]=[CH:33]/[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40](=[O:48])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C@@:20]([OH:31])([CH2:28][CH2:29][OH:30])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:18])[CH2:14][OH:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].ClCCl.[C:52](OC(=O)C)(=[O:54])[CH3:53].N1[CH:64]=[CH:63]C=CC=1.[OH2:65]>>[C:52]([O:30][CH2:29][CH2:28][C@:20]([OH:31])([C@@H:19]([C:17](=[O:18])[NH:16][C@H:13]([CH2:14][O:15][C:63](=[O:65])[CH3:64])[CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=1)/[CH:32]=[CH:33]/[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40](=[O:48])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])(=[O:54])[CH3:53]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 118260148HCID 118260148, compound

Product 1

HCID 118260146HCID 118260146, compoundYield 96%

Procedure

To a mixture of No. 6801976, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-hydroxymethyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (304 mg, 0.45 mmol) and dichloromethane (15 mL) were added acetic anhydride (129 μL, 1.36 mmol) and pyridine (10 μL, 0.12 mmol), and the mixture was stirred at room temperature for 6 hours. Water was added and the mixture was extracted with dichloromethane, and dried over anhydrous sodium sulfate. The filtrate was then concentrated under reduced pressure. The resulting residue was left in a refrigerator overnight to obtain No. 6801977, tert-butyl (E)-(2S,3S)-2-(2-acetoxy-ethyl)-3-[(S)-1-acetoxymethyl-2-(4-but-2-ynyloxy-phenyl)-ethylcarbamoyl]-2-hydroxy-12-oxo-nonadec-4-enoate (328 mg, 96% yield, ESI (LC/MS positive mode) m/z 757 (M+H); Rt 3.37 min.). Formic acid (15 mL) was added to No. 6801977 (328 mg, 0.43 mmol) and the mixture was stirred at room temperature for 4 hours. After confirming the consumption of the starting materials by LCMS, formic acid was distilled off under reduced pressure. The residue was purified by preparative HPLC to obtain the title compound (35 mg, 11% yield, yellow oil).

Workup

  1. additionTo a mixture of No
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe filtrate was then concentrated under reduced pressure
  5. waitThe resulting residue was left in a refrigerator overnight
  6. customto obtain No

Sources & evidence

ORD record
ord-43a79c88417f49ac8d3aea3e8201cf45
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

Loading…