(C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OCH2Ph → (C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OH

HRID 1246735Notes

Reaction equation

HRID 1246735 reaction equation
[N:1]([C:38]([CH2:40][O:41][CH2:42][C:43]([NH:45][CH2:46][C:47]([NH:49][CH2:50][C:51]([NH:53][CH2:54][C:55]([O:57]CC1C=CC=CC=1)=[O:56])=[O:52])=[O:48])=[O:44])=[O:39])([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[H][H]>C(O)C.[Pd]>[N:1]([C:38]([CH2:40][O:41][CH2:42][C:43]([NH:45][CH2:46][C:47]([NH:49][CH2:50][C:51]([NH:53][CH2:54][C:55]([OH:57])=[O:56])=[O:52])=[O:48])=[O:44])=[O:39])([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 101159097(C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OCH2PhHCID 178418361HCID 178418361, compound

Product 1

HCID 85817110(C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OHYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OCH2Ph (1.0 g, 1.1 mmol) was dissolved in absolute ethanol (100 mL), 10% Pd/C (0.2 g) was added, and this mixture was shaken under 70 psi hydrogen pressure for 3 h in a Parr apparatus. The reaction mixture was heated to reflux and filtered through a celite layer and the solvent was evaporated under reduced pressure to leave (C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OH as a white solid (0.86 g, 96%), mp 163–164° C. 1H-NMR (300 MHz, δ, CD3OD): 0.90 (6H, t, J=6.9 Hz), 1.29 (64H, m), 1.57 (4H, bs), 3.21 (2H, t, J=7.8 Hz), 3.35 (2H, t, J=7.8 Hz), 3.93 (2H, s), 3.94 (2H, s), 3.97 (2H, s), 4.12 (2H, s), 4.40 (2H, s). IR (KBr, cm−1): 1740 (CO), 1650 (CO).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered through a celite layer
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-597bf46351cb499fbac509a79c4bb8e3
Source dataset
uspto-grants-2006_10
Patent number
US07129208B2

Reaction notes

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