Dicyclohexylcarbodiimide → HCID 69962623, compound

HRID 743886Notes

Reaction equation

HRID 743886 reaction equation
C[O:2][C:3](=[O:21])[C@H:4]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[NH:5][C:6](OCC1C=CC=CC=1)=[O:7].[N:22]1[NH:23][N:24]=[N:25][C:26]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:51]=[CH:50][C:36]2[N:37]([CH:40]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])C(O)=O)[CH:38]=[N:39][C:35]=2[CH:34]=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>>[O:7]=[C:6]([NH:5][C@H:4]([C:3]([OH:21])=[O:2])[CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH:40]([N:37]1[C:36]2[CH:50]=[CH:51][C:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[C:26]3[N:25]=[N:24][NH:23][N:22]=3)=[CH:34][C:35]=2[N:39]=[CH:38]1)[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 7018803HCID 7018803, compoundHCID 158381802-[5-[2-(2H-tetrazol-5-yl)phenyl]benzimidazol-1-yl]octanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 69962623HCID 69962623, compoundYield 13.9%

Procedure

N-carbobenzyloxy-L-Lysine methyl ester (1.0 mmoles, 0.295 g) and 2-[5-[2-(2H-tetrazol-5-yl)phenyl]-1H-benzimidazol-1-yl]octanoic acid (1.0 moles, 0.405 g) were reacted with 1.0 moles of hydroxybenzotriazole and dicyclohexylcarbodiimide as in Example 37. The stereoisomers were separated on silica gel eluted with 5% EtOH in chloroform with 1% acetic acid. Each was hydrolyzed with sodium hydroxide as in Example 37 and hydrogenated to remove the carbobenzyloxy group in ethanol over 5% Pd/C for 4 hours. The catalyst was removed by filtering through celite. The solvent was removed in vacuo to yield 74 mg of N-[1-Oxo-2-[5-[2-(2H-tetrazol-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-lysine. Isomer A (MS)

Workup

  1. customThe stereoisomers were separated on silica gel
  2. washeluted with 5% EtOH in chloroform with 1% acetic acid
  3. customEach was hydrolyzed with sodium hydroxide as in Example 37 and hydrogenated to remove the carbobenzyloxy group in ethanol over 5% Pd/C for 4 hours
  4. customThe catalyst was removed
  5. filtrationby filtering through celite
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8b1f04e0f0f946b0992119001d72a1c9
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

Loading…