HCID 71736092, compound → HCID 71736093, compound

HRID 1053598Notes

Reaction equation

HRID 1053598 reaction equation
[OH:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1>Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:23][CH2:24][O:25][C:26]2[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=2)[C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:15]=2)=[CH:33][CH:34]=1

Participants

3

Reactant 1

HCID 71736092HCID 71736092, compound

Product 1

HCID 71736093HCID 71736093, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound 27 (60 mg, 0.13 mmol) was refluxed in concentrated hydrochloric acid for 2 hours. The reaction was concentrated, quenched with 50 mL of water, and neutralized with ammonium hydroxide to pH 7. The mixture was then extracted with EtOAc and the combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated to yield the compound 28 (50 mg, 0.11 mmol, 85% yield). 1H NMR (CDCl3, 400 MHz) δ12.00 (bs, 1H), 8.92 (bs, 2H), 6.98 (d, J=8.0 Hz, 2H), 6.66-6.77 (m, 10H), 3.99-5.05 (m, 4H), 3.72 (t, J=5.6 Hz, 4H), 2.44 (t, J=7.2 Hz, 2H), 2.17 (t, J=7.2 Hz, 2H), 1.72 (q, J=7.2, 7.6 Hz, 2H); HRMS (ESI, positive) m/z calcd. for C26H30NO6 [M+H]+: 452.2073, found: 452.2007.

Workup

  1. concentrationThe reaction was concentrated
  2. customquenched with 50 mL of water
  3. extractionThe mixture was then extracted with EtOAc
  4. washthe combined organic layer was washed with water
  5. dry with materialbrine, and dried over Na2SO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e20e7cbcde744d0d8f7075cc1bf618af
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

Loading…