Triethylamine → HCID 86750501, compound

HRID 976103Notes

Reaction equation

HRID 976103 reaction equation
C1(N(C2C=CC=CC=2)[C:8]([N:10]2[CH2:15][CH2:14][C@@H:13]([C:16]([N:18]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:17])[CH2:12][C@@H:11]2[C:29]([OH:31])=O)=[O:9])C=CC=CC=1.[CH:38]1[CH:39]=[CH:40][C:41]2[N:46](O)N=N[C:42]=2[CH:43]=1.CCN=C=N[CH2:53][CH2:54][CH2:55]N(C)C.F[C:60](F)(F)[C:61](O)=O.[CH2:66]([O:73][C:74]([N:76]([CH2:80][C:81]([NH2:83])=[O:82])[CH2:77][CH2:78][NH2:79])=[O:75])[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1.[CH2:84](N(CC)CC)C>C(Cl)Cl>[C:53]1([N:46]([C:41]2[CH:40]=[CH:39][CH:38]=[CH:43][CH:42]=2)[C:8]([N:10]2[CH2:15][CH2:14][C@@H:13]([C:16]([N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:17])[CH2:12][C@@H:11]2[C:29]([NH:79][CH2:78][CH2:77][N:76]([C:74]([O:73][CH2:66][C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)=[O:75])[CH2:80][C:81]([NH2:83])=[O:82])=[O:31])=[O:9])[CH:54]=[CH:55][CH:61]=[CH:60][CH:84]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67724760HCID 67724760, compoundHCID 70083324HCID 70083324, compound

Product 1

HCID 86750501HCID 86750501, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.076 g (0.15 mmole) of trans 1-(N,N-diphenylaminocarbonyl)-4-(RS)-(N,N-dipentylaminocarbonyl)piperidine -2-(RS)-carboxylic acid (from Example 1, Step E above) and 0.022 g (0.165 mmole) of HOBt in 6 mL of dry methylene chloride at 0 deg C. under nitrogen was treated with 0.04 g (0.21 mmole) of EDAC. The cooling bath was removed and after 40 mina mixture of 0.11 g (0.3 mmole) of N-(benzyloxycarbonyl)-N-(aminocarbonylmethyl)ethylenediamine trifluoroacetic acid salt (from Example 3, Step C above) and 0.042 mL (0.3 mmole) of triethylamine in 2 mL of methylene chloride was added, and the resulting solution was stirred for 19 hr at room temperature. The mixture was then concentrated in vacuo and the residue partitioned between 20 mL of water and 30 mL of ethyl acetate. The layers were separated and the aqueous layer was extracted with 25 mL of ethyl acetate. The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on 36 g of silica eluting with 1 L of 3:100 methanol:methylene chloride then 250 mL of 4:100 methanol:methylene chloride to give 56 mg (50%) of an oil.

Workup

  1. customat 0 deg C
  2. customThe cooling bath was removed
  3. additionwas added
  4. concentrationThe mixture was then concentrated in vacuo
  5. customthe residue partitioned between 20 mL of water and 30 mL of ethyl acetate
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with 25 mL of ethyl acetate
  8. dry with materialThe combined organic layers were dried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography on 36 g of silica eluting with 1 L of 3:100 methanol

Sources & evidence

ORD record
ord-020298b03c8f4bb98ef485669efeeb48
Source dataset
uspto-grants-1997_03
Patent number
US05610165

Reaction notes

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