Lithium Hydroxide → HCID 131723374, compound

HRID 2228380Notes

Reaction equation

HRID 2228380 reaction equation
C([O:3][C:4](=[O:27])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]=[CH2:26])=[CH:20][CH:19]=1)[N:6]([SiH:14]([CH3:16])[CH3:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C.[Li+].[OH-]>C1COCC1.O>[C:7]([N:6]([SiH:14]([CH3:16])[CH3:15])[C@H:5]([C:4]([OH:27])=[O:3])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH:25]=[CH2:26])=[CH:22][CH:23]=1)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 131723375HCID 131723375, compound

Product 1

HCID 131723374HCID 131723374, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

The same procedure as described for 5 Scheme 2 was followed except that (Boc)2O was used instead of FmocCl for protection of the amine group; Colorless oil (yield=64%); 1H NMR (300 MHz, CDCl3) δ 0.24 (s, 6 H), 1.19 (t, J=7.14 Hz, 3 H), 1.39 (s, 9 H), 1.72 (d, J=11.1 Hz, 2 H), 3.04 (m, 2 H), 4.13 (t, J=7.14 Hz, 2 H), 4.54 (m, 1 H), 4.79 (m, 1 H), 4.83 (m, 1 H), 5.07 (bd, NH, 1 H); 13C NMR (75 MHz, CDCl3) −3.4 (2C), 14.1, 23.6, 28.3 (3C), 38.4, 54.4, 61.2, 79.7, 113.4, 128.8 (3C), 133.8 (2C), 134.5, 137.0, 155.1, 171.9. (b) N-Boc-4-allyldimethylsilylphenylalanine ethyl ester (190 mg, 0.5 mmol) was hydrolyzed with a LiOH (60 mg, 2.5 mmol) in THF/H2O (5:1, 15 mL) for 4 h at room temperature. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate (20 mL). After neutralization of the solution with acetic acid and concentration, the residue was purified by column chromatography (5:1 ethyl acetate/MeOH) to afford a viscous solid (144 mg, 82%); 1H NMR (300 MHz, CDCl3) δ 0.29 (s, 6 H), 1.41 (s, 9 H), 1.76 (d, J=7.68 Hz, 2 H), 3.05-3.32 (2 H), 4.48 (m, 1 H), 4.86 (m, 1 H), 4.91 (m, 1 H), 5.80 (m, 1 H), 7.24 (d, J=7.29 Hz, 2 H), 7.47 (d, J=7.29 Hz, 2 H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate (20 mL)
  3. concentrationAfter neutralization of the solution with acetic acid and concentration
  4. customthe residue was purified by column chromatography (5:1 ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-d035419fd0bd4c5b84bd16e1b57c94fa
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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