Hydrochloric Acid → HCID 178484437, compound

HRID 1352519Notes

Reaction equation

HRID 1352519 reaction equation
[O:1]=[S:2]1(=[O:37])[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][CH2:26][N:27]([C:29]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])[CH3:28])=[CH:20][CH:19]=2)[C:13]([O:15]C)=[O:14])=[N:3]1.[Li+].[OH-].Cl.O>C1COCC1.CO.O>[O:1]=[S:2]1(=[O:37])[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][CH2:26][N:27]([C:29]([CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)=[O:30])[CH3:28])=[CH:20][CH:19]=2)[C:13]([OH:15])=[O:14])=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 178501388HCID 178501388, compound

Product 1

HCID 178484437HCID 178484437, compoundYield 42%

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 42%. MS (ES) 513 (M+, 100%).

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-4ea3a1ce816a49098eb8030e2d0d4273
Source dataset
uspto-grants-2007_05
Patent number
US07220766B2

Reaction notes

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