Lithium hydroxide, monohydrate → HCID 10432719, compound

HRID 2294740Notes

Reaction equation

HRID 2294740 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:35])[C@H:7]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[NH:8][C:9](=[O:25])[CH2:10][C:11]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])([CH3:13])[CH3:12]>O.O1CCOCC1>[CH2:18]([O:17][C:15]([NH:14][C:11]([CH3:13])([CH3:12])[CH2:10][C:9]([NH:8][C@H:7]([C:6]([OH:35])=[O:5])[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)=[O:25])=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10026366HCID 10026366, compound

Product 1

HCID 10432719HCID 10432719, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

0.184 g (4.39 mmol) of lithium hydroxide hydrate dissolved in 8 ml of water is added dropwise to a solution of 1.7 g (3.84 mmol) of N-[3-[1-(benzyloxy)formamido]-3-methylbutyryl]-3-(p-methoxyphenyl)-L-alanine methyl ester in 16 ml of dioxan. The solution is stirred at 0° for 1 hour, then treated with 20 ml of water and extracted twice with ether. The aqueous phase is acidified with 6N hydrochloric acid and extracted twice with ether. The combined ether extracts are washed with saturated sodium chloride solution, dried over sodium sulphate and then evaporated under reduced pressure. N-[3-[1-(Benzyloxy)formamido]-3-methylbutyryl]-3-(p-methoxyphenyl)-L-alanine is obtained as a colourless oil, MS: 429 (M+H)+.

Workup

  1. extractionextracted twice with ether
  2. extractionextracted twice with ether
  3. washThe combined ether extracts are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0eaab0bb252f4f46986de6e2a8dc6503
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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