Hydrochloric Acid → HCID 68493275, compound

HRID 2242457Notes

Reaction equation

HRID 2242457 reaction equation
C([O:3][C:4]([C:6]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:14](=[O:24])[CH:13]1[CH:9]([CH2:10][CH:11]([O:25][C:26]3[C:35]4[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=4)[N:29]=[C:28]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:27]=3)[CH2:12]1)[C:8](=[O:44])[NH:7]2)=[O:5])C.CO.Cl>O1CCCC1.O>[CH3:37][O:36][C:32]1[CH:31]=[C:30]2[C:35]([C:26]([O:25][CH:11]3[CH2:10][CH:9]4[CH:13]([C:14](=[O:24])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][CH:22]5[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]4=[O:44])[CH2:23]5)[CH2:12]3)=[CH:27][C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[N:29]2)=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68493128HCID 68493128, compound

Product 1

HCID 68493275HCID 68493275, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Compound 92 (95 mg, 0.159 mmol) was dissolved in tetrahydrofuran (10 ml), methanol (5 ml) and water (4 ml) Lithium hydroxide (40 mg, 1.67 mmol) was dissolved in water (1 ml) and added. The reaction mixture was heated to 65° C. After 3 h the reaction mixture was cooled, acidified with aqueous HCl (pH=5), evaporated on silica and purified by silica gel chromatography (10% MeOH in dichloromethane→15% MeOH in dichloromethane) to give the pure title product (65 mg, 72%). MS (M+H+): 569.8

Workup

  1. additionadded
  2. temperatureAfter 3 h the reaction mixture was cooled
  3. customevaporated on silica
  4. custompurified by silica gel chromatography (10% MeOH in dichloromethane→15% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-b3e3f1bdb11440ab86cac93380b02e1b
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

Loading…