Picolinic acid → (2S,3R,4R,5S)-2,5-Di-(N-((2-pyridinyl)carbonyl)amino)-3,4-dihydroxy-1,6-diphenylhexane

HRID 847637Notes

Reaction equation

HRID 847637 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[NH2:10][C@H:11]([C@@H:19]([OH:31])[C@H:20]([OH:30])[C@@H:21]([NH2:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N=[C:33]=[NH:34]>C(Cl)(Cl)Cl>[N:34]1[CH:33]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:10][C@H:11]([C@@H:19]([OH:31])[C@H:20]([OH:30])[C@@H:21]([NH:29][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9]

Participants

5

Reactant 3

HCID 1018Picolinic acidHCID 160435CarbodiimideHCID 10990240(2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane

Product 1

HCID 22845614(2S,3R,4R,5S)-2,5-Di-(N-((2-pyridinyl)carbonyl)amino)-3,4-dihydroxy-1,6-diphenylhexane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Picolinic acid was coupled to the resultant compound of Example 171 using the carbodiimide coupling procedure described in Example 55 to provide, after chromatography on silica gel using 5% methanol in chloroform, 58 mg (60%) of the desired compound (Rf 0.6, 10% methanol in chloroform) as a white solid, m.p. 179°-184° C. Mass spectrum: (M+H)+ =511.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-d234bc7101ac4fb9b45f5b13fe63eab2
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

Loading…