Water → HCID 90060337, compound

HRID 1779246Notes

Reaction equation

HRID 1779246 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:32]=[CH:33]/[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]2([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])OCC[O:41]2)[C@@:22]([OH:31])([CH3:30])[C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].O.FC(F)(F)C(O)=O>ClCCl>[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:32]=[CH:33]/[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40](=[O:41])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C@@:22]([OH:31])([CH3:30])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 90060336HCID 90060336, compound

Product 1

HCID 90060337HCID 90060337, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,3S,E)-tert-Butyl 3-((S)-3-(4-(but-2-ynyloxy)phenyl)-1-methoxy-1-oxopropan-2-ylcarbamoyl)-11-(2-heptyl-1,3-dioxolan-2-yl)-2-hydroxy-2-methylundec-4-enoate (540 mg, 0.756 mmol) was dissolved in dichloromethane (3.5 mL), and water (0.35 mL) was added. Trifluoroacetic acid (10 mL) was added and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated. The residue was then purified by diol column chromatography (n-hexane/acetone) to obtain the target compound as pale yellow oil at a yield of 91%.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customThe residue was then purified by diol column chromatography (n-hexane/acetone)

Sources & evidence

ORD record
ord-a7eb4fa637ca44af97b239f21e84bfb8
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

Loading…