Hydrochloric Acid → L-Leucine, L-leucyl-, methyl ester, hydrochloride (1:1)

HRID 2298446Notes

Reaction equation

HRID 2298446 reaction equation
[ClH:1].[NH:2](C(OC(C)(C)C)=O)[C@H:3]([C:8]([NH:10][C@H:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].C(OCC)(=O)C>COC(C)(C)C>[NH2:2][C@H:3]([C:8]([NH:10][C@H:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH:13]([CH3:14])[CH3:15])=[O:9])[CH2:4][CH:5]([CH3:6])[CH3:7].[ClH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 7073357Boc-leu-leu-ome

Product 1

HCID 15598024L-Leucine, L-leucyl-, methyl ester, hydrochloride (1:1)Yield 95.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Gaseous HCl (10.2 g, 279 mmol) was infused into a mixture of Boc-Leu-Leu-OMe (17.9 g, 50.0 mmol) and ethyl acetate (71.4 g) at 20 to 25° C. After 30 min, t-butyl methyl ether (142.9) was added to the resulting solution followed by a seed crystal. The resulting solid crystalline product was filtered at 0 to 5° C. and dried in vacuo to give H-Leu-Leu-OMe.HCl (14.1 g, 95.7%).

Workup

  1. filtrationThe resulting solid crystalline product was filtered at 0 to 5° C.
  2. customdried in vacuo

Sources & evidence

ORD record
ord-368ee0751a4a42b4abe06ffe4aa340a9
Source dataset
uspto-grants-2002_12
Patent number
US06492490B1

Reaction notes

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