Benzyl N3,N7,N12,N16-tetra(t-butoxycarbonyl)-3,7,12,16-tetraazahexadecanoate → N3,N7,N12,N16-Tetra(t-butoxycarbonyl)-3,7,12,16-tetraazahexadecanoic acid

HRID 1397112Notes

Reaction equation

HRID 1397112 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:20][CH2:21][CH2:22][N:23]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:9][C:10]([O:12]CC1C=CC=CC=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]([CH2:20][CH2:21][CH2:22][N:23]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86666525Benzyl N3,N7,N12,N16-tetra(t-butoxycarbonyl)-3,7,12,16-tetraazahexadecanoate

Product 1

HCID 11006845N3,N7,N12,N16-Tetra(t-butoxycarbonyl)-3,7,12,16-tetraazahexadecanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 30 (1.56 g, 2.08 mmol) in MeOH (21 mL) was degassed with argon for 10 min followed by the addition of 10% Pd/C (400 mg). The mixture was then stirred under an atmosphere of hydrogen for 3 h. The mixture was filtered through glassfiber filter paper and the filtrate was concentrated under reduced pressure to give crude 31 (1.37 g, 100%) as a colourless liquid that was used without purification: 1H NMR (400 MHz, acetone-d6): δ 1.40 (bs, 9H), 1.44-1.46 (m, 27H), 1.52 (bs, 4H), 1.66-1.83 (m, 4H), 3.06 (bt, J=5.6, 2H), 3.22-3.32 (m, 10H), 3.94 (s, ½ of 2H, rotomer A), 3.97 (s, ½ of 2H, rotamer B), 5.98 (bs, 1H).

Workup

  1. filtrationThe mixture was filtered through glassfiber
  2. filtrationfilter paper
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9a488dba9aa54294bbce9dd3a55d888d
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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