Pyridine → HCID 145857710, compound

HRID 723223Notes

Reaction equation

HRID 723223 reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[CH3:14][Si:15]([CH3:57])([CH3:56])[CH2:16][CH2:17][O:18][C:19](=[O:55])[NH:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([C:37]3[CH:41]=[C:40]([C:42]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[NH:43])[S:39][C:38]=3[S:52][CH3:53])(=[O:36])=[O:35])[CH:29]=2)=[C:23]([NH2:54])[CH:22]=1.N1C=CC=CC=1.[CH3:64][O:65][C:66](=[O:80])[C:67]1[CH:72]=[CH:71][C:70]([O:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][NH2:79])=[CH:69][CH:68]=1>C(Cl)Cl.CCOC(C)=O.C(N(CC)CC)C>[CH3:64][O:65][C:66](=[O:80])[C:67]1[CH:68]=[CH:69][C:70]([O:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][NH:79][C:2]([NH:54][C:23]2[CH:22]=[C:21]([NH:20][C:19]([O:18][CH2:17][CH2:16][Si:15]([CH3:14])([CH3:56])[CH3:57])=[O:55])[CH:26]=[C:25]([CH3:27])[C:24]=2[C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([C:37]3[CH:41]=[C:40]([C:42]([NH:44][C:45]([O:47][C:48]([CH3:50])([CH3:51])[CH3:49])=[O:46])=[NH:43])[S:39][C:38]=3[S:52][CH3:53])(=[O:35])=[O:36])[CH:29]=2)=[O:3])=[CH:71][CH:72]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 57532225Methyl 4-[(5-aminopentyl)oxy]benzoateHCID 145857641HCID 145857641, compound

Product 1

HCID 145857710HCID 145857710, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitrophenyl chloroformate (99.2 mg, 0.49 mmol) was added to a solution of {2-amino-3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester (303 mg, 0.45 mmol, Example 294: step f) and pyridine (39.8 μL, 0.49 mmol) in methylene chloride (5 mL) at rt. The reaction mixture was stirred for 2 hrs at rt. 4-(5-Amino-pentyloxy)-benzoic acid methyl ester (117 mg, 0.49 mmol, Example 283: step b) and triethylamine were added to the reaction mixture and stirred for 2 hrs at rt. The reaction mixture was diluted in EtOAc, washed with water and brine, and dried over magnesium sulfate. Removal of solvents in vacuo was followed by flash chromatography (50–60% EtOAc/hexanes) to afford the title compound as a yellow solid (280 mg, 66.5%). ESI-MS (m/z): Calcd. for C44H57N5O10S3Si: 940.3 (M+1); found: 939.9.

Workup

  1. stirringstirred for 2 hrs at rt
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of solvents in vacuo

Sources & evidence

ORD record
ord-957a5254deeb43fabf601b368dff6b78
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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