HCID 14016132, compound → HCID 11153871, compound

HRID 2379180Notes

Reaction equation

HRID 2379180 reaction equation
[OH:1][C@@H:2]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:4][OH:5]>C(OCC)(=O)C.[Pd]>[OH:1][C@@H:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:4][OH:5]

Participants

4

Reactant 1

HCID 14016132HCID 14016132, compound

Product 1

HCID 11153871HCID 11153871, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution comprising 2.49 g (6.08 mmole) of tert-Butyl (1S, 2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecynyl]carbamate, Herold, Chim. Acta. 71: 354, 1988, and 20 mg of 20% Pd on carbon in 50 ml of ethyl acetate was hydrogenated on a Parr shaker at 3 atmospheres for 3 hours. The reaction mixture was filtered through Celite and the solvent removed under reduced pressure yielding tert-Butyl (1S, 2S)-N-[2-hydroxy-1-(hydroxymethyl) heptadecyl]carbamate having a mass of 2.53 g and of approximately 100%. Tert-Butyl (1S, 2S)-N-[2-hydroxy-1-(hydroxymethyl) heptadecyl]carbamate is a wax having a melting point of approximately 45° to 56° C. A 1H NMR analysis of the compound at 300 MHz using CDCl3 comprised the following peaks: δ0.887 (3H, t, J=6.7 Hz), 1.261 (26H, bs), 1.460 (9H, s), 2.054 (2H, bs), 3.589 (1H, bs), 3.820 (2H, bs), 3.941 (1H, bs) and 5.232 (1H, d, J=8.0 Hz). E;elemental analysis calculated for C23H47NO4 comprised the following constituents: C: 68.78, H: 11.79, N: 3.49. The values obtained experimentally comprised: C: 68.46,H: 11.71, N: 3.44.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4b033862085c4614be3ebb4ff54f64ca
Source dataset
uspto-grants-1994_11
Patent number
US05360818

Reaction notes

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