Triethylamine → N-[4'-(tert-butyl-diphenyl-silanyloxy)-3'-methoxy-biphenyl-2-yl]-2-(4-chlorophenyl)-2-prop-2-ynyloxy-acetamide

HRID 1375222Notes

Reaction equation

HRID 1375222 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:18][CH2:19][C:20]#[CH:21])[C:15]([OH:17])=O)=[CH:10][CH:9]=1.[C:22]([Si:26]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[NH2:40])=[CH:30][C:29]=1[O:41][CH3:42])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>ClCCl.C(Cl)(Cl)Cl.CN(C)C=O>[C:22]([Si:26]([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[NH:40][C:15](=[O:17])[CH:14]([C:11]2[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=2)[O:18][CH2:19][C:20]#[CH:21])=[CH:30][C:29]=1[O:41][CH3:42])([CH3:25])([CH3:23])[CH3:24]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 112480034'-(tert-Butyl-diphenyl-silanyloxy)-3'-methoxy-biphenyl-2-ylamineHCID 23075515(4-Chloro-phenyl)-prop-2-ynyloxy-acetic acid

Product 1

HCID 21079853N-[4'-(tert-butyl-diphenyl-silanyloxy)-3'-methoxy-biphenyl-2-yl]-2-(4-chlorophenyl)-2-prop-2-ynyloxy-acetamide

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (4.3 g, 33 mmol) is added to a solution of (4-chlorophenyl-prop-2-ynyloxy-acetic acid (6.8 g, 30 mmol) in a mixture of 150 ml of dichloromethane and few drops of N,N-dimethylformamide. The reaction mixture is stirred for 4 hours at room temperature and then added to a solution of 4′-(tert-butyl-diphenyl-silanyloxy)-3′-methoxy-biphenyl-2-ylamine (13.8 g, 30 mmol) and triethylamine (4.6 g, 45 mmol) in 150 ml of dichloromethane. The resulting mixture is stirred for 16 hours at room temperature under a nitrogen atmosphere. Subsequently, the mixture is diluted with chloroform and extracted with water. The combined organic layer is dried over sodium sulfate and evaporated and the remaining crude product is subjected to flash-chromatography (ethyl acetate/hexane 3;7) yielding N-[4′-(tert-butyl-diphenyl-silanyloxy)-3′-methoxy-biphenyl-2-yl]-2-(4-chlorophenyl)-2-prop-2-ynyloxy-acetamide as an orange oil.

Workup

  1. stirringThe resulting mixture is stirred for 16 hours at room temperature under a nitrogen atmosphere
  2. extractionextracted with water
  3. dry with materialThe combined organic layer is dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-34da988b67dd4c79acc430f95f08405f
Source dataset
uspto-grants-2007_01
Patent number
US07166746B2

Reaction notes

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