Sodium Hydroxide → HCID 57133944, compound

HRID 351474Notes

Reaction equation

HRID 351474 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10](=[CH:11][O:12]C)[CH2:9][CH2:8][N:7]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6]1)=[O:4].[OH-].[Na+]>C1COCC1.Cl>[CH3:1][O:2][C:3]([C:5]1([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:10]([CH:11]=[O:12])[CH2:9][CH2:8][N:7]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53798186HCID 53798186, compound

Product 1

HCID 57133944HCID 57133944, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound of Example 200, Step B (3.02 g, 8.26 mmol) in THF (40 mL) and 10% aqueous HCl solution (40 mL) was allowed to stir at room temperature for 14 h. The solution was adjusted to pH 9 with 5N NaOH and extracted twice with CH2Cl2. The combined organic layers were washed with a saturated aqueous brine solution, dried over Na2SO4, filtered and concentrated under vacuum. Purification by silica gel chromatography employing 3-5% EtOAc/CH2Cl2 as the eluant afforded the compound of Example 200, Step C as a mixture of isomers (1.89 g): +APcl MS (M+1)+352; 1H NMR (400 MHz, CDCl3) δ: 9.82 and 9.81 (s, 1H), 7.02-7.45 (arom, series of m, 10 H), 3.64 and 3.60 (s, 3H).

Workup

  1. extractionextracted twice with CH2Cl2
  2. washThe combined organic layers were washed with a saturated aqueous brine solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-064f14cbecef439885cc12b2bacc896a
Source dataset
uspto-grants-2004_06
Patent number
USRE038524E1

Reaction notes

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