Hydrochloric Acid → HCID 10098780, compound

HRID 1265228Notes

Reaction equation

HRID 1265228 reaction equation
[C:1]1([CH3:39])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([NH:12][C@H:13]([C:35]([O:37]C)=[O:36])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29]([NH:31][CH2:32][CH2:33][CH3:34])=[O:30])[CH:23]=2)=[CH:18][CH:17]=1)(=[O:11])=[O:10].[OH-].[Na+].Cl>C(O)(C)C>[C:1]1([CH3:39])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([NH:12][C@H:13]([C:35]([OH:37])=[O:36])[CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29]([NH:31][CH2:32][CH2:33][CH3:34])=[O:30])[CH:23]=2)=[CH:20][CH:21]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59050121HCID 59050121, compound

Product 1

HCID 10098780HCID 10098780, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

The compound of Example 19 (60.0 mg, 0.11, 1 equiv) was dissolved in isopropanol (3.0 mL) and treated with a 1 M aqueous solution of NaOH (1 mL). The reaction mixture was warmed to 60° C. and stirred for 4 hours. It was acidified with a 0.1 M aqueous solution of HCl to pH 2 and cooled to 4° C. overnight. The white precipitate of the title compound was filtered off and dried under vacuum. Yield 30.0 mg, 51.3%. 1H NMR (DMSO; 200 MHz) δ 13.99 (broad s, 1H); 8.50 (s, 2H); 7.71 (s, 1H); 7.49 (d, 2H); 7.25 (d, 2H); 7.15-7.12 (m, 1H); 7.00 (s, 2H); 6.88 (d, 2H); 6.23-6.09 (m, 1H); 4.19-4.03 (m, 3H); 3.21-2.93 (m, 1H); 2.59 (s, 6H); 2.21 (3H), 1.43 (quin, 2H); 0.97 (t, 3H). MS (ESI) 540 (M+H).

Workup

  1. temperaturecooled to 4° C. overnight
  2. filtrationThe white precipitate of the title compound was filtered off
  3. customdried under vacuum

Sources & evidence

ORD record
ord-aed23d9e2cfe4e83b32397a2a5f8169d
Source dataset
uspto-grants-2003_04
Patent number
US06545029B2

Reaction notes

Loading…