Hydrochloric Acid → HCID 67353870, compound

HRID 75805Notes

Reaction equation

HRID 75805 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10](=[O:35])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21]([C:23]([NH:25][CH:26]([CH:31]([CH3:33])[CH3:32])[C:27]([O:29]C)=[O:28])=[O:24])[O:20][N:19]=2)=[CH:14][C:13]=1[CH3:34].[Li+].[OH-].Cl>C1COCC1.O>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[NH:9][C:10](=[O:35])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21]([C:23]([NH:25][CH:26]([CH:31]([CH3:32])[CH3:33])[C:27]([OH:29])=[O:28])=[O:24])[O:20][N:19]=2)=[CH:14][C:13]=1[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67353219HCID 67353219, compound

Product 1

HCID 67353870HCID 67353870, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of the crude compound of step 8, LiOH (3.0 equiv.) and 50 ml of 5:1 THF/water was stirred at room temperature for 15 minutes. The reaction mixture was slightly acidified to pH <7 by adding 2N HCl and then evaporated to dryness under vacuum. The residue was dissolved in a chloroform and methanol mixture, adsorbed on silica (100-200 mesh) and purified by flash chromatography on silica gel, and then eluted with 2-15% methanol in chloroform to provide the title compound as a pale green solid after drying in vacuo; 1H NMR (300 MHz, DMSO-d6) δ: 0.85-0.88 (d, J=6.6 Hz, 6H), 2.14-2.19 (m, 1H), 2.34 (s, 3H), 3.92-3.96 (m, 1H), 7.11-7.16 (m, 2H), 7.24-7.31 (m, 1H), 7.60 (S, 1H), 7.67-7.70 (d, J=8.7 Hz, 1H), 7.76 (s, 1H), 8.01-8.04 (m, 2H), 8.86 (s, 1H), 9.24 (s, 1H); ms (ESI) m/z 473.2 [M+H]+.

Workup

  1. customevaporated to dryness under vacuum
  2. dissolutionThe residue was dissolved in a chloroform and methanol mixture
  3. custompurified by flash chromatography on silica gel
  4. washeluted with 2-15% methanol in chloroform

Sources & evidence

ORD record
ord-65e5091f26c2488584911af5e0500066
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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