Lithium hydroxide, monohydrate → N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucine

HRID 2393049Notes

Reaction equation

HRID 2393049 reaction equation
[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([O:17]C)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].O.[OH-].[Li+]>CO.O>[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 7237624Z-Leu-Leu methyl ester

Product 1

HCID 7299379N-((Phenylmethoxy)carbonyl)-L-leucyl-L-leucineYield 90.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirred solution of N-Cbz-L-Leu-L-Leu-OCH3 (6.0 g, 14.6 mmol) in MeOH/H2O (3:1) (60 mL) at R. T. was added lithium hydroxide monohydrate (LiOH.H2O) (1.0 g, 43.9 mmol) and hydrogen peroxide H2O2 (30% weight in H2O) (4.5 mL, 43.9 mmol). The reaction mixture was stirred for 3.5 h and then quenched with 10% HCl. The resulting mixture was extracted with EA (3×20 mL). The combined organic extracted were washed with sat. NaCl (2×10 mL), dried (MgSO4) and concentrated in vacuo to afford N-Cbz-L-Leu-L-Leu-OH as a white solid (5.0 g, 90.5%): 1H NMR (CDCl3, 300 MHz) δ 0.89-0.92 (t, 12 H, J=3.0 Hz), 1.48-1.71 (m, 6 H), 4.11-4.13 (m, 1 H), 4.55-4.62 (m, 1 H), 5.09 (s, 2 H), 5.64 (d, 1 H, J=9.0 Hz), 6.83 (d, 1 H, J=9.0 Hz), 7.33-7.40 (m, 5 H) ppm.

Workup

  1. customquenched with 10% HCl
  2. extractionThe resulting mixture was extracted with EA (3×20 mL)
  3. extractionThe combined organic extracted
  4. washwere washed with sat. NaCl (2×10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8515d16bf7a54ec283317b69fe4f9dd4
Source dataset
uspto-grants-1998_09
Patent number
US05804560

Reaction notes

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