Ether hydrochloride → HCID 70404184, compound

HRID 986614Notes

Reaction equation

HRID 986614 reaction equation
[C:1]12([O:11][C:12](=[O:26])[C@@H:13]([CH3:25])[NH:14]C(OCC3C=CC=CC=3)=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[ClH:27].CCOCC>CO.[Pd]>[ClH:27].[C:1]12([O:11][C:12](=[O:26])[C@@H:13]([CH3:25])[NH2:14])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

5

Reactant 2

HCID 10953452Ether hydrochlorideHCID 14031642HCID 14031642, compound

Product 1

HCID 70404184HCID 70404184, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-Benzyloxycarbonyl-D-alanine 1-adamantyl ester (7.35 g, 20.6 mmol) was dissolved in 100 mL MeOH and 14.5 mL 1.25N HCl/ether. The solution was hydrogenated over 1.09 g of 10% Pd/C at 40 psi in a Parr apparatus at room temperature for 40 minutes. The solution was filtered through a Celite pad and the clear filtrate was evaporated to dryness to give a yellow oil, which was crystallized from EtOAc. A light yellow salt (4.2 g) was obtained. The crude product was recrystallized from MeOH-EtOAc; yielded 7.85 g (72%), mp 218°-219° (dec), 250 MHz nmr (CD3OD, ppm) 1.50 (d, 3H, J=7.35 Hz, β--CH3 of Ala), 1.72 (m, 6H, 1-adamantyl aliphatic protons of C's 2, 8 and 9), 2.18 (m, 9H, adamantyl aliphatic protons), 3.95 (q, 1H, J=7.35 Hz, α--H of Ala).

Workup

  1. filtrationThe solution was filtered through a Celite pad
  2. customthe clear filtrate was evaporated to dryness
  3. customto give a yellow oil, which
  4. customwas crystallized from EtOAc

Sources & evidence

ORD record
ord-81c47c0d8e694e22a0e6ad3d5d5423cd
Source dataset
uspto-grants-1987_12
Patent number
US04714619

Reaction notes

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