L-Valine → HCID 18659791, compound

HRID 1291773Notes

Reaction equation

HRID 1291773 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](Cl)=[O:7].[NH2:9][C@H:10]([C:14]([OH:16])=[O:15])[CH:11]([CH3:13])[CH3:12]>O1CCOCC1.[OH-].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([NH:9][C@H:10]([C:14]([OH:16])=[O:15])[CH:11]([CH3:13])[CH3:12])=[O:7]

Participants

5

Reactant 2

HCID 6287L-ValineHCID 694002-Methoxyethyl chloroformate

Product 1

HCID 18659791HCID 18659791, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3.06 g (22.1 mmol) of chloroformic acid (2-methoxy-ethyl) ester in 18 ml of dioxane is added to 2.59 g (22.1 mmol) of L-valine in 26.4 ml of 2N NaOH and the mixture is then stirred for 18 h at RT. The reaction mixture is extracted with chloroform, and the inorganic phase is acidified with 4N HCl and extracted again with chloroform. The chloroform phase last obtained is dried and concentrated by evaporation to yield the title compound: 1H-NMR (200 MHz, CDCl3): 0.92 and 0.99 (2 d, J=7 Hz, 6H), 2.2 (m, 1H), 3.38 (s, 3H), 3.59 and 4.24 (2m, each 2H), 4.3 (m, 1H), 5.4 (d, J=9 Hz, HN), 8.5 (sb, 1H).

Workup

  1. extractionThe reaction mixture is extracted with chloroform
  2. extractionextracted again with chloroform
  3. customThe chloroform phase last obtained
  4. customis dried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3dc093c4fbb0426686fe831cbfd6139f
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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