Hydrochloric Acid → HCID 178525544, compound

HRID 220138Notes

Reaction equation

HRID 220138 reaction equation
[C:1]12([CH:11]([OH:37])[CH2:12][O:13][C:14]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([C@H:25]5[CH2:30][CH2:29][C@H:28]([CH2:31][C:32]([O:34]CC)=[O:33])[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[NH:16][N:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.[OH-].[Li+].O1CCCC1.Cl>O>[C:1]12([CH:11]([OH:37])[CH2:12][O:13][C:14]3[CH:18]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]([C@H:25]5[CH2:26][CH2:27][C@H:28]([CH2:31][C:32]([OH:34])=[O:33])[CH2:29][CH2:30]5)=[CH:23][CH:24]=4)[NH:16][N:15]=3)[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178471764HCID 178471764, compound

Product 1

HCID 178525544HCID 178525544, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A scintillation vial was charged with the product from Example 1G (18 mg, 0.036 mmol), lithium hydroxide monohydrate (5 mg, 0.12 mmol) and a mixed solvent (2 mL of tetrahydrofuran, 1 mL of H2O). The reaction vessel was placed in a shaker at room temperature overnight. After this time the mixture was acidified with 10% HCl, concentrated, and purified via RP-HPLC (Preparative reversed-phase high pressure liquid chromatography) using a Zorbax SB-C18 7 μM 21.2×250 mm column with UV detection analyzed at 220 and 254 nM (preparative method: water with 0.1% trifluoroacetic acid and CH3CN with 0.1% trifluoroacetic acid gradient 5-95% CH3CN over 30 minutes at 15 mL/min.) to provide the title product. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.12 (m, 2H), 1.42-1.86 (m, 19H), 1.94 (m, 3H), 2.14 (d, J=7.01 Hz, 2H), 2.47 (m, 1H), 3.89 (dd, J1=10.38 Hz, J2=7.94 Hz, 1H), 4.24 (dd, J1=10.68 Hz, J2=2.74 Hz, 1H), 4.70 (d, J=5.49 Hz, 2H), 6.07 (s, 1H), 7.28 (d, J=8.24 Hz, 2H), 7.59 (d, J=8.24 Hz, 2H), 12.13 (br s, 2H); MS (ESI) m/z 479.3 [M+H]+.

Workup

  1. concentrationconcentrated
  2. custompurified via RP-HPLC (Preparative reversed-phase high pressure liquid chromatography)
  3. customanalyzed at 220 and 254 nM (preparative method: water with 0.1% trifluoroacetic acid and CH3CN with 0.1% trifluoroacetic acid gradient 5-95% CH3CN over 30 minutes at 15 mL/min.)

Sources & evidence

ORD record
ord-757354f35fd043be9e2f75c5715316ac
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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