Diethyl 2-t-butoxycarbonylamino-13-benzyloxycarbonyl-1,14-tetradecanedicarboxylate → Diethyl 2-t-butoxycarbonylamino-13-carboxy-1,14-tetradecanedicarboxylate

HRID 21982Notes

Reaction equation

HRID 21982 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:33]([O:35]CC1C=CC=CC=1)=[O:34])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:33]([OH:35])=[O:34])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 19930809Diethyl 2-t-butoxycarbonylamino-13-benzyloxycarbonyl-1,14-tetradecanedicarboxylate

Product 1

HCID 19930832Diethyl 2-t-butoxycarbonylamino-13-carboxy-1,14-tetradecanedicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl 2-t-butoxycarbonylamino-13-benzyloxycarbonyl-1,14-tetradecanedicarboxylate (5.0 g, 8.87 mmol) is dissolved in ethyl acetate (150.0 mL), and 10% Pd-C (2.6 g) is added. The reaction flask is put under an atmosphere of hydrogen and stirred for 2 hours. The product is then filtered through a pad of Celite, and the solvent is evaporated to give diethyl 2-t-butoxycarbonylamino-13-carboxy-1,14-tetradecanedicarboxylate.

Workup

  1. filtrationThe product is then filtered through a pad of Celite
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-fc9ac6c888b94c3792d8c3411a404b3f
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Reaction notes

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