Hydrochloric Acid → HCID 58798624, compound

HRID 500373Notes

Reaction equation

HRID 500373 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([O:21]C)=[O:20])[C:10]([S:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCCC1.O.C(OCC)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([OH:21])=[O:20])[C:10]([S:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])([CH3:11])[CH3:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58798622HCID 58798622, compound

Product 1

HCID 58798624HCID 58798624, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.52 g (25.7 mmol) of N-tert-butoxycarbonyl-3-(4-pentenylthio)-L-valine, methyl ester in 200 mL of tetrahydrofuran at room temperature was added a solution of 1.10 g (26.2 mmol) of lithium hydroxide monohydrate in 50 mL of water. The resulting mixture was stirred at room temperature for 65 hours. To the reaction mixture then was added 28 mL of 1.00N hydrochloric acid. The mixture was diluted with diethyl ether, washed with water (3×) and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to afford 8.10 g of N-tert-butoxycarbonyl-3-(4-pentenylthio)-L-valine as a colorless oil. NMR (300 MHz, CDCl3): δ 5.75 (d of d of t, 1H, J=17.2, 10.3, 6.6 Hz), 5.40 (br s, 1H), 5.05-4.94 (m, 2H), 4.28 (br s, 1H), 2.56 (m, 2H), 2.13 (quart., 2H, J=7.3Hz), 1.63 (quint., 2H, J=7.3Hz), 1.44 (s, 9H), 1.39 (s, 3H), 3 H).

Workup

  1. washwashed with water (3×) and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5bc429d1b8e84d3a86e98637faa43de3
Source dataset
uspto-grants-2010_08
Patent number
US07772183B2

Reaction notes

Loading…