Pyridine → HCID 86652487, compound

HRID 2364922Notes

Reaction equation

HRID 2364922 reaction equation
[CH:1]1([CH:7]=[CH:8][C:9]2[C:10](=[O:24])[NH:11][C:12](=[O:23])[N:13]([CH:22]=2)[C@@H:14]2[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[CH2:15]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[CH3:31][O:32][C:33]1[CH:54]=[CH:53][C:36]([C:37](Cl)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)=[CH:35][CH:34]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.CO>[CH:1]1([CH:7]=[CH:8][C:9]2[C:10](=[O:24])[NH:11][C:12](=[O:23])[N:13]([CH:22]=2)[C@@H:14]2[O:21][C@H:18]([CH2:19][O:20][C:37]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)([C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)[C:36]3[CH:35]=[CH:34][C:33]([O:32][CH3:31])=[CH:54][CH:53]=3)[C@@H:16]([OH:17])[CH2:15]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 67117228HCID 67117228, compound

Product 1

HCID 86652487HCID 86652487, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

Compound (2b) (320 mg, 0.95 mmol) was azeotroped three times with anhydrous pyridine. The mixture was added with anhydrous pyridine (1.5 ml) and 4,4′-dimethoxytrityl chloride (380 mg, 1.12 mmol), and subsequently with DMAP (41 mg, 0.34 mmol). Finally, triethylamine (160 μl, 1.14 mmol) was added and the mixture was stirred for 21 hours at room temperature. After characterization by TLC (CHCl3:MeOH=9:1), the product was purified using a silica gel column with the development solvent of CHCl3 and MeOH while varying the ratio of CHCl3:MeOH from 98:2 to 95:5 to obtain the target Compound (3b) as a pale yellow solid (329 mg, 0.52 mmol, yield 54%). The target compound was determined by 1H NMR for identification. Further, mass analysis was carried out by MALDI-TOF MS and it was identified as the target compound (calcd. for C38H43N2O7 [M+H]+ 639.306, found 639.496).

Workup

  1. customAfter characterization by TLC (CHCl3:MeOH=9:1), the product was purified

Sources & evidence

ORD record
ord-c1fdfaf4473f48d28c17e3e18ca708f3
Source dataset
uspto-grants-2014_04
Patent number
US08697357B2

Reaction notes

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