Hydrochloric Acid → HCID 178525807, compound

HRID 1352521Notes

Reaction equation

HRID 1352521 reaction equation
[O:1]=[S:2]1(=[O:36])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([NH:11][C@@H:12]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:29]4[O:30][CH2:31][CH2:32][O:33][C:28]=4[CH:27]=3)=[CH:20][CH:19]=2)[C:13]([O:15]C)=[O:14])=[N:3]1.[Li+].[OH-].Cl.O>C1COCC1.CO.O>[O:36]=[S:2]1(=[O:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([NH:11][C@@H:12]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:29]4[O:30][CH2:31][CH2:32][O:33][C:28]=4[CH:27]=3)=[CH:22][CH:23]=2)[C:13]([OH:15])=[O:14])=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 178501378HCID 178501378, compound

Product 1

HCID 178525807HCID 178525807, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The crude product from Step A 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 48%.

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-f3fdf41d9e0f407ebd0f80e646b2bef2
Source dataset
uspto-grants-2007_05
Patent number
US07220766B2

Reaction notes

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