Hydrochloric Acid → HCID 18512315, compound

HRID 1370934Notes

Reaction equation

HRID 1370934 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:46]=[CH:45][C:25]([O:26][C:27]2[CH:44]=[CH:43][C:30]([O:31][CH2:32][CH2:33][CH2:34][C:35]([NH:37][CH2:38][C:39]([O:41]C)=[O:40])=[O:36])=[CH:29][CH:28]=2)=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH2:1]([N:8]([CH2:21][C:22]1[CH:46]=[CH:45][C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]([O:31][CH2:32][CH2:33][CH2:34][C:35]([NH:37][CH2:38][C:39]([OH:41])=[O:40])=[O:36])=[CH:43][CH:44]=2)=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18512362HCID 18512362, compound

Product 1

HCID 18512315HCID 18512315, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 251A was treated with 22N aqueous sodium hydroxide: 1 tetrahydrofuran: 1 ethanol (2 ml) at room temperature overnight. The reaction mixture acidified with 1N hydrochloric acid to pH 3-4, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue purified by HPLC to provide the titled compound. 1H NMR (500 MHz, DMSO-d6) δ12.13-12.81 (br.s, 1 H), 8.94 (s, 1 H), 8.18 (t, 1 H), 7.14-7.34 (m, 7 H), 6.98 (m, 7 H), 6.82 (d, 2 H), 4.05 (s, 2 H), 4.00 (s, 2 H), 3.95 (t, 2 H), 3.74 (d, 2 H), 2.91 (s, 3 H), 2.38 (s, 3 H), 2.30 (t, 2 H), 1.93 (m, 2 H); MS (ESI+) m/z 632 (M+H)+.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue purified by HPLC

Sources & evidence

ORD record
ord-2bea8c4db4e946b3b43b07424b3e9206
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

Loading…