Pyridine → HCID 67116970, compound

HRID 2364920Notes

Reaction equation

HRID 2364920 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH:6][CH3:7].[C@@H:8]1([N:16]2[CH:23]=[CH:22][C:20](=[O:21])[NH:19][C:17]2=[O:18])[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1.N1C=CC=CC=1.[CH3:30][O:31][C:32]1[CH:53]=[CH:52][C:35]([C:36](Cl)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)=[CH:34][CH:33]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.CO>[CH3:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2][CH3:1].[CH3:44][O:43][C:40]1[CH:39]=[CH:38][C:37]([C:36]([O:14][CH2:13][C@H:12]2[O:15][C@@H:8]([N:16]3[CH:23]=[CH:22][C:20](=[O:21])[NH:19][C:17]3=[O:18])[CH2:9][C@@H:10]2[OH:11])([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:35]2[CH:52]=[CH:53][C:32]([O:31][CH3:30])=[CH:33][CH:34]=2)=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 67117307HCID 67117307, compound

Product 1

HCID 67116970HCID 67116970, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

Compound (2a) (340 mg, 1.05 mmol) was azeotroped three times with anhydrous pyridine. The mixture was added with anhydrous pyridine (2.0 ml) and 4,4′-dimethoxytrityl chloride (427 mg, 1.26 mmol) which has been deaerated for 1 hour, and subsequently with DMAP (38 mg, 0.31 mmol). Finally, triethylamine (170 μl, 1.26 mmol) was added and the mixture was stirred for 13 hours at room temperature. After characterization by TLC (CHCl3:MeOH=95:5), the product was purified with silica gel column chromatography using 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 (3a) as a pale yellow solid (304 mg, 0.49 mmol, yield 46%). 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 C37H43N2O7 [M+H]+ 627.306, found 627.455).

Workup

  1. customAfter characterization by TLC (CHCl3:MeOH=95:5), the product was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-7de14aa621314eeca424394a69766dcb
Source dataset
uspto-grants-2014_04
Patent number
US08697357B2

Reaction notes

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