4-Aminobenzoic Acid → HCID 178448921, compound

HRID 1655590Notes

Reaction equation

HRID 1655590 reaction equation
NC1C=CC(C(O)=O)=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:22]([N:26]([C:64]1[CH:74]=[CH:73][C:67]([C:68]([O:70]CC)=[O:69])=[CH:66][CH:65]=1)[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:40]2[N:44](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:43]=[N:42][N:41]=2)=[CH:30][CH:29]=1)[CH2:23][CH2:24][CH3:25]>>[CH2:22]([N:26]([C:64]1[CH:65]=[CH:66][C:67]([C:68]([OH:70])=[O:69])=[CH:73][CH:74]=1)[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:40]2[NH:44][N:43]=[N:42][N:41]=2)=[CH:32][CH:33]=1)[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 6101p-Toluenesulfonic acidHCID 19791885HCID 19791885, compound

Product 1

HCID 178448921HCID 178448921, compound

Procedure

The title compound was prepared in analogy to Example 164 starting from 4-aminobenzoic acid instead of 3-aminobenzoic acid. Tosic acid deprotection of ethyl 4-{N-butyl-N-[(2'-[N-triphenylmethyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}benzoate followed by ester hydrolysis afforded, after purification by flash chromatography on silica gel eluting with 95:5:0.25 chloroform/ethanol/acetic acid, the title compound (100 mg, 26%) as a solid. 1H NMR (CD3OD, 300 MHz) δ 1.00 (t, 3H), 1.40 (m, 2H), 1.65 (m, 2H), 3.50 (t, 2HO, 4.65 (s, 2H), 6.70 (m, 2H), 7.10 (m, 2H), 7.20 (m, 2H), 7.55 (m, 2H), 7.65 (m, 2H), 7.80 (m, 2H). MS (DCl/NH3) m/e 428 (M+H)+, 445 (M+H+NH3)+.

Workup

  1. customafforded
  2. customafter purification by flash chromatography on silica gel eluting with 95:5:0.25 chloroform/ethanol/acetic acid

Sources & evidence

ORD record
ord-30cf89dc0ea146ddb5b7b38bc9a2ddf5
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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