Triethylamine → HCID 18647013, compound

HRID 728763Notes

Reaction equation

HRID 728763 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][N:16]1[C:31](=[O:32])[C:30]([CH3:33])=[CH:29][N:18]([C@@H:19]2[O:25][C@H:22]([CH2:23][OH:24])[C@@H:21]([N:26]=[N+:27]=[N-:28])[CH2:20]2)[C:17]1=[O:34].CCN(CC)CC>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([NH:13][CH2:14][CH2:15][N:16]2[C:31](=[O:32])[C:30]([CH3:33])=[CH:29][N:18]([C@@H:19]3[O:25][C@H:22]([CH2:23][OH:24])[C@@H:21]([N:26]=[N+:27]=[N-:28])[CH2:20]3)[C:17]2=[O:34])=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 54075093HCID 54075093, compound

Product 1

HCID 18647013HCID 18647013, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 10 mg 3-(4-hydroxyphenyl)-propionic acid N-hydroxysuccinimideester (HPP:NOS) in MeOH was mixed with 10 mg of 3-AE-AZT (Example 27) dissolved in 100 ul MeOH. The mixture was stirred 30 minutes at room temperature, followed by addition of 2.5 ul of Et3N. This mixture was incubated overnight at room temperature, and then chromatographed by TLC on silica gel-F 250 um using the solvent system CHCl3 /MeOH/HOAc (90+10+1). The following Rf values were observed upon visualization by UV at 254 nm: 3-AE-AZT, 0.034;NOS, 0.28; product, 0.35; HPPA, 0.37; andHPP:NOS, 0.55. The product, unlike 3-(4-hydroxyphenyl)propionic acid (HPPA), was an effective inhibitor of polarization in a FPIA for AZT.

Workup

  1. waitThis mixture was incubated overnight at room temperature
  2. customchromatographed by TLC on silica gel-F 250 um

Sources & evidence

ORD record
ord-69ad5f849bdd4b7eb5bcabbc5f035350
Source dataset
uspto-grants-1991_09
Patent number
US05051361

Reaction notes

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