2-[4-(Benzyloxy)phenyl]-5-n-butyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]-methyl]-3H-1,2,4-triazol-3-one → HCID 178441904, compound

HRID 36236Notes

Reaction equation

HRID 36236 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19](=[O:20])[N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]4[N:38](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:37]=[N:36][N:35]=4)=[CH:24][CH:23]=3)[C:17]([CH2:58][CH2:59][CH2:60][CH3:61])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:19](=[O:20])[N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]4[NH:35][N:36]=[N:37][N:38]=4)=[CH:24][CH:23]=3)[C:17]([CH2:58][CH2:59][CH2:60][CH3:61])=[N:16]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 199393732-[4-(Benzyloxy)phenyl]-5-n-butyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]-methyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 178441904HCID 178441904, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Deprotection of 2-[4-(benzyloxy)phenyl]-5-n-butyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one in 75% aqueous acetic acid was accomplished by the procedure of Example 5, Step C, except that the mixture was kept at 60° C. overnight. After work-up, the residue was flash chromatographed over silica gel (10 mL for 0.05 mmole; gradient elution with 2-5-10% methanol in CH2Cl2) to give a 43% yield of the title compound as a glassy solid, homogeneous by TLC in 10% MeOH/CH2Cl2 ; mass spectrum (FAB) m/e 558 (M+1)+.

Workup

  1. customchromatographed over silica gel (10 mL for 0.05 mmole; gradient elution with 2-5-10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-10ec092b950f4132bdf8bc5a4b51ff8d
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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