Methanol → HCID 3011035, compound

HRID 1379400Notes

Reaction equation

HRID 1379400 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:15]([NH:17][C@H:18]([C@@H:26]([OH:45])[C@H:27]([OH:44])[C@@H:28]([NH:36][C:37](=[O:43])[C@H:38]([CH:40]([CH3:42])[CH3:41])[NH2:39])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH:12]([CH3:14])[CH3:13].N=[C:47]=[NH:48].[CH3:49][OH:50]>C(Cl)(Cl)Cl>[N:48]1[CH:47]=[CH:4][CH:3]=[CH:2][C:7]=1[C:49]([NH:10][C@H:11]([C:15]([NH:17][C@H:18]([C@@H:26]([OH:45])[C@H:27]([OH:44])[C@@H:28]([NH:36][C:37](=[O:43])[C@H:38]([CH:40]([CH3:41])[CH3:42])[NH:39][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH:12]([CH3:14])[CH3:13])=[O:50]

Participants

6

Reactant 4

HCID 887MethanolHCID 1018Picolinic acidHCID 160435CarbodiimideHCID 10368652HCID 10368652, compound

Product 1

HCID 3011035HCID 3011035, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Picolinic acid was coupled to the resultant compound of Example 173 using the carbodiimide coupling procedure described in Example 55 to provide after silica gel chromatography using a gradient of 5-10% methanol in chloroform, the desired compound (Rf 0.16, 10% methanol in chloroform) as a white solid, m.p. 167°-171° C., in 61% yield. Mass spectrum: (M+H)+ =709.

Workup

  1. customto provide after silica gel chromatography

Sources & evidence

ORD record
ord-e8f59690d8a34f1683cc5ae47b5680d4
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

Loading…