Hydrochloric Acid → HCID 11684862, compound

HRID 1866195Notes

Reaction equation

HRID 1866195 reaction equation
[CH:1]1([C:7]([N:9]([CH3:37])[CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C@H:20]([NH:25][C:26]3[S:27][CH:28]=[C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:30]=3)[C:21]([O:23]C)=[O:22])=[CH:15][CH:14]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].Cl.O>C1COCC1.CO.O>[CH:1]1([C:7]([N:9]([CH3:37])[CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C@H:20]([NH:25][C:26]3[S:27][CH:28]=[C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:30]=3)[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 11577251HCID 11577251, compound

Product 1

HCID 11684862HCID 11684862, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The crude product from Step B was dissolved in a THF/MeOH/H2O mixture (6:0.1:1; 2 ml). Aqueous 1M LiOH solution (1.6 ml) was added and the mixture was stirred for 3 days at room temperature. Then the reaction mixture was neutralized with 1M HCl, a small amount of water was added and the mixture extracted with ethyl acetate. The solvent was evaporated. The product was purified by chromatography (SiO2, ethyl acetate/hexane). The yield was 42%.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. customThe solvent was evaporated
  3. customThe product was purified by chromatography (SiO2, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-18e97ee295754a75876fcc34d851df95
Source dataset
uspto-grants-2009_12
Patent number
US07629370B2

Reaction notes

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