BOC-LEU-PRO-OH synthesis

10synthesis methods

Product Name:BOC-LEU-PRO-OH
CAS Number:64205-66-9
Molecular formula:C16H28N2O5
Molecular Weight:328.4

L-Proline, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-, methyl ester

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64205-66-9
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Yield:64205-66-9 100%

Reaction Conditions:

with lithium hydroxide monohydrate in tetrahydrofuran;methanol;water; for 0.5 h;

Steps:

(S)-Methyl 2-((S)-1-((S)-2-(tert-butoxycarbonylamino)-4-methylpentanoyl)pyrrolidine-2-carboxamido)-4-methylpentanoate (S3)

The compound S2 (1.63 g, 4.75 mmol) was taken with THF (70 ml) and MeOH (7 ml). A solution of LiOH.H₂O (2.00 g, 47.51 mmol) in H₂O (31 ml) was added dropwise ultimately attaining a molarity of 1.5M. The reaction mixture was stirred for about 30 min. The solvent was removed, acidified to pH 4 at 0 °C, extracted with ethyl acetate. The organic layer was washed with water and brine to yield the acid (1.56 g, 4.75 mmol) in quantitative yield.

References:

Ghosh, Keshab Ch;Duttagupta, Indranil;Bose, Chandra;Banerjee, Priyanjalee;Gayen, Anuran Kumar;Sinha, Surajit [Synthetic Communications,2019,vol. 49,# 2,p. 221 - 236] Location in patent:supporting information