Hydrochloric Acid → HCID 58938722, compound

HRID 2038542Notes

Reaction equation

HRID 2038542 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:19][CH:20]1[CH2:22][CH2:21]1)[CH:13]([OH:18])[C:14]([O:16]C)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C1COCC1.O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:19][CH:20]1[CH2:21][CH2:22]1)[CH:13]([OH:18])[C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58938711HCID 58938711, compound

Product 1

HCID 58938722HCID 58938722, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the methyl ester of Step 2 (400 mg; 1.3 mmol) in THF (8 mL) and water (6.63 mL) was added LiOH (1 N; 1.37 mL). The reaction mixture was stirred for 30 minutes and then acidified with 1.0 N HCl to pH=3˜4. The mixture was extracted with EtOAc (20 mL, twice). The combined organic layer was washed with water, brine, and then concentrated in vacuo to afford the title compound (370 mg). (M+1) 294.

Workup

  1. extractionThe mixture was extracted with EtOAc (20 mL
  2. washThe combined organic layer was washed with water, brine
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d52bced11da648bc852bc70bdce1f606
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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