Hydrochloric Acid → HCID 54012151, compound

HRID 355335Notes

Reaction equation

HRID 355335 reaction equation
[CH2:1]([C@@H:4]([C@@:9]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])([CH2:11][CH:12]([CH3:14])[CH3:13])[CH3:10])[C:5]([O:7]C)=[O:6])[CH:2]=[CH2:3].[OH-].[K+].Cl>CO>[CH2:1]([C@@H:4]([C@@:9]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])([CH2:11][CH:12]([CH3:14])[CH3:13])[CH3:10])[C:5]([OH:7])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57252150HCID 57252150, compound

Product 1

HCID 54012151HCID 54012151, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

221 mg of the methyl ester from Step 1 are hydrolyzed by treatment with 5 mL of 1N KOH and 5 mL of MeOH for 4 hours at room temperature. The solution is made acidic with 1N HCl. Most of the MeOH is removed and the product is extracted into EtOAC. The product is purified by flash chromatography on silica gel using 70% hexanes/28% EtOAc/2% HOAc to give the title compound.

Workup

  1. customMost of the MeOH is removed
  2. extractionthe product is extracted into EtOAC
  3. customThe product is purified by flash chromatography on silica gel using 70% hexanes/28% EtOAc/2% HOAc

Sources & evidence

ORD record
ord-3ab8c762bc8a428dbd9b690c68ce639e
Source dataset
uspto-grants-1998_11
Patent number
US05830869

Reaction notes

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