Lithium Hydroxide → HCID 70122734, compound

HRID 2227896Notes

Reaction equation

HRID 2227896 reaction equation
C([O:3][C:4](=[O:38])[C@H:5]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:18][CH:17]=1)[NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[OH-].[Li+]>C(O)C.O.C(OCC)(=O)C>[C:7]([NH:6][C@H:5]([C:4]([OH:38])=[O:3])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:20][CH:21]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 70122199HCID 70122199, compound

Product 1

HCID 70122734HCID 70122734, compoundYield 96.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-benzoyl-O-dodecanylthioethyl-L-tyrosine ethyl ester (4.2 g, 7.75 mmol) in ethanol (50 ml) was added a solution of lithium hydroxide (0.42 g, 10.08 mmol) in water (5 ml). The solution was stirred at room temperature for 4 hours and then diluted with ethyl acetate and washed with 1N hydrochloric acid and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (3.84 g, 96%) as a white solid.

Workup

  1. washwashed with 1N hydrochloric acid and brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4af75bcc8d124f70bb7dbadb08145db6
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

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