Hydrochloric Acid → HCID 18512035, compound

HRID 1370960Notes

Reaction equation

HRID 1370960 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:51]=[CH:50][C:25]([O:26][C:27]2[CH:28]=[C:29]([CH:47]=[CH:48][CH:49]=2)[O:30][CH2:31][CH2:32][CH2:33][C:34]([N:36]2[CH2:41][CH2:40][CH2:39][CH:38]([C:42]([O:44]CC)=[O:43])[CH2:37]2)=[O:35])=[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+].C(O)C.Cl>C(OCC)(=O)C.O1CCCC1>[CH2:1]([N:8]([CH2:21][C:22]1[CH:51]=[CH:50][C:25]([O:26][C:27]2[CH:28]=[C:29]([CH:47]=[CH:48][CH:49]=2)[O:30][CH2:31][CH2:32][CH2:33][C:34]([N:36]2[CH2:41][CH2:40][CH2:39][CH:38]([C:42]([OH:44])=[O:43])[CH2:37]2)=[O:35])=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 18512294HCID 18512294, compound

Product 1

HCID 18512035HCID 18512035, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 279A was treated with 2N NaOH aqueous solution (1 mL), ethyl alcohol (0.5 mL) and tetrahydrofuran (0.5 mL) at room temperature overnight. 1N hydrochloric acid was dropped to the reaction mixture until pH=2˜3. Ethyl acetate (3 mL) was used to extract the product. The organic layer was separated, dried (Na2SO4), concentrated in vaccuo, and purified by HPLC to provide the titled compound. 1H NMR (500 MHz, DMSO-d6) δ12.03-12.70 (br.s, 1 H), 8.95 (s, 1 H), 7.24 (m, 8 H), 7.04 (m, 1 H), 6.94 (m, 4 H), 6.69 (m, 1 H), 6.49 (m, 2 H), 4.06 (s, 2 H), 4.03 (s, 2 H), 3.94 (t, J=6.4 Hz, 2 H), 3.82 (m, 1 H), 3.72 (m, 1 H), 3.31 (dd, J=13.6, 9.2 Hz, 1 H), 2.98 (t, J=11.1 Hz, 1 H), 2.91 (s, 3 H), 2.38 (m, 5 H), 2.24 (m, 1 H), 1.90 (m, 3 H), 1.65 (m, 1 H), 1.52 (m, 1 H), 1.34 (m, 1 H); MS (APCI+) m/z 686.1 (M+H)+.

Workup

  1. extractionto extract the product
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vaccuo
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-8e3549b870c946ffa448bb6207b2d7ae
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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