Water → HCID 90060203, compound

HRID 1779242Notes

Reaction equation

HRID 1779242 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:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]2([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])OCC[O:44]2)[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[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>C(O)=O>[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:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](=[O:44])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[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

4

Reactant 2

HCID 962WaterHCID 90060258HCID 90060258, compound

Product 1

HCID 90060203HCID 90060203, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

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-(2-methoxyethyl)-undec-4-enoate (1.619 g, 2.136 mmol) was dissolved in formic acid (8.0 mL), and water (420 μL) was added. The reaction mixture was stirred at room temperature for 24 hours, and concentrated. After subsequently repeating twice the operation of dissolution in ethyl acetate and concentration, the residue was purified by diol column chromatography (dichloromethane/ethyl acetate) to obtain the target compound at a yield of 80%.

Workup

  1. concentrationconcentrated
  2. dissolutionthe operation of dissolution in ethyl acetate
  3. concentrationconcentration
  4. customthe residue was purified by diol column chromatography (dichloromethane/ethyl acetate)
  5. customto obtain the target compound at a yield of 80%

Sources & evidence

ORD record
ord-8d1df80a4f804d04b561a6cdca4f835b
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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