Lithium hydroxide, monohydrate → HCID 53928063, compound

HRID 1656051Notes

Reaction equation

HRID 1656051 reaction equation
[C:1]([S:5][CH2:6][C:7]1([C:17]([NH:19][C@H:20]([C:28]([O:30]C)=[O:29])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:18])[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>CO>[C:1]([S:5][CH2:6][C:7]1([C:17]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:18])[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131718219HCID 131718219, compound

Product 1

HCID 53928063HCID 53928063, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve N-[[1,2,3,4-tetrahydro-2-[[(t-butyl)thio]methyl]-2-naphthalenyl]carbonyl]-L-phenylalanine, methyl ester (158 mg, 0.36 mmol) in methanol (3 mL). Add a solution of lithium hydroxide hydrate (1 mL in water, 1 mmol) and stir at room temperature under argon overnight. Partition between 1N hydrochloric acid and methylene chloride. Separate the organic phase and extract the acidic phase with methylene chloride (2×10 mL). Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo to give the title compound (149 mg, 97%).

Workup

  1. customPartition between 1N hydrochloric acid and methylene chloride
  2. customSeparate the organic phase
  3. extractionextract the acidic phase with methylene chloride (2×10 mL)
  4. dry with materialCombine the organic phases, dry (MgSO4)
  5. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-94e7ee9f36ed4364b82b13cffb25a29f
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Reaction notes

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