Hydrochloric Acid → HCID 10813990, compound

HRID 1720350Notes

Reaction equation

HRID 1720350 reaction equation
[CH2:1]([O:5][C:6](=[O:35])[C@H:7]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[NH:8][C:9]([C:11]1([NH:16][C:17](=[O:26])[C@@H:18]([S:22]C(=O)C)[CH:19]([CH3:21])[CH3:20])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([O:5][C:6](=[O:35])[C@H:7]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[NH:8][C:9]([C:11]1([NH:16][C:17](=[O:26])[C@@H:18]([SH:22])[CH:19]([CH3:20])[CH3:21])[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10529589HCID 10529589, compound

Product 1

HCID 10813990HCID 10813990, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a degasseal solution of N-[[1-[(2-(S)-acetylmercapto-3-methyl-1-oxobutyl)-amino]-1-cyclopentyl]-carbonyl]-L-tyrosine n-butyl ester (2.4 g, 4.74 mmole) in methanol at 0° C. is added dropwise 1N sodium hydroxide (4.74 ml, 4.74 mmole). The mixture is stirred for 30 minutes, neutralized to pH 3 with 1N hydrochloric acid and concentrated to dryness. The residue is dissolved in a mixture of water and ethyl acetate. The organic phase is separated, washed with brine, dried over magnesium sulfate and evaporated to dryness to yield N-[[1-[(2-(S)-mercapto-3-methyl- 1-oxobutyl)amino]- 1-cyclopentyl]-carbonyl]-L-tyrosine n-butyl ester, m.p. 182°-183° C.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue is dissolved in a mixture of water and ethyl acetate
  3. customThe organic phase is separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-dc2a9f727d464b4ba2ccf3641cb526f2
Source dataset
uspto-grants-1996_04
Patent number
US05506244

Reaction notes

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