Hydrochloric Acid → HCID 7146200, compound

HRID 1863919Notes

Reaction equation

HRID 1863919 reaction equation
C[O:2][C:3](=[O:23])[C@@H:4]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=1[F:22])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].O1CCCC1.[OH-].[Li+].Cl>CO>[C:9]([O:8][C:6]([NH:5][C@@H:4]([C:3]([OH:23])=[O:2])[CH2:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=1[F:22])=[O:7])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 11450415HCID 11450415, compound

Product 1

HCID 7146200HCID 7146200, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.41 g (7.5 mmol) of (R)-N-(tert-butoxycarbonyl)-2,4,5-trifluorophenylalanine methyl ester in approximately 200 mL of a mixture of tetrahydrofuran:methanol: 1N lithium hydroxide (3:1:1) was stirred at 50° C. for 4 h. The reaction was cooled, acidified with 5% hydrochloric acid (aqueous) and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated in vacuo to give the title compound. LC-MS 220.9 (M+1-BOC).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c48d7e5ad6884f56b0c92d6bbc95bf9e
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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