Triethylamine → HCID 67507701, compound

HRID 877889Notes

Reaction equation

HRID 877889 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C@@H:6]1[C@H:10]([O:11][Si](C(C)(C)C)(C)C)[C@@H:9]([C@@H:19]([CH3:21])[OH:20])[O:8][C@H:7]1[N:22]1[CH:29]=[C:28]([CH3:30])[C:26](=[O:27])[NH:25][C:23]1=[O:24].[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.F.F.F.C(N(CC)CC)C.C(N(CC)CC)C>C1COCC1.CCOC(C)=O>[CH3:45][O:44][C:41]1[CH:40]=[CH:39][C:38]([C:37]([O:20][C@H:19]([CH3:21])[C@H:9]2[O:8][C@@H:7]([N:22]3[CH:29]=[C:28]([CH3:30])[C:26](=[O:27])[NH:25][C:23]3=[O:24])[C@H:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[C@@H:10]2[OH:11])([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:36]2[CH:53]=[CH:54][C:33]([O:32][CH3:31])=[CH:34][CH:35]=2)=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 67506454HCID 67506454, compound

Product 1

HCID 67507701HCID 67507701, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Compound 11 (0.42 g, 0.96 mmol) was mixed with 4,4′-dimethoxytrityl chloride (0.82 g, 2.41 mmol) and dried over P2O5 under reduced pressure. The mixture was dissolved in anhydrous pyridine (3 mL) and stirred at 45° C. for 18 h under an atmosphere of argon. The reaction mixture was cooled to room temperature and diluted with EtOAc (40 mL) and washed with saturated aqueous NaHCO3 (60 mL) and brine (40 mL), dried over Na2SO4, filtered and concentrated. The residue obtained was purified by silica gel column chromatography and eluted first with 50% EtOAc in hexanes and then with 5% methanol in CH2Cl2. The product obtained was dissolved in a mixture of triethylamine trihydrofluoride (1.38 mL, 8.44 mmol) and triethylamine (0.58 mL, 4.22 mmol) in THF (8.4 mL). After 72 h the mixture was diluted with EtOAc (60 mL), washed with water (40 mL), saturated aqueous NaHCO3 (40 mL) and brine (40 mL) then dried over Na2SO4, filtered and evaporated. The residue obtained was purified by silica gel column chromatography and eluted with 70% EtOAc in hexanes to yield Compound 12 (0.44 g, 73%). ES MS m/z 631.2 [M+H]+.

Workup

  1. dry with materialdried over P2O5 under reduced pressure
  2. dissolutionThe mixture was dissolved in anhydrous pyridine (3 mL)
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additiondiluted with EtOAc (40 mL)
  5. washwashed with saturated aqueous NaHCO3 (60 mL) and brine (40 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography
  11. washeluted first with 50% EtOAc in hexanes
  12. customThe product obtained
  13. washwashed with water (40 mL), saturated aqueous NaHCO3 (40 mL) and brine (40 mL)
  14. dry with materialthen dried over Na2SO4
  15. filtrationfiltered
  16. customevaporated
  17. customThe residue obtained
  18. customwas purified by silica gel column chromatography
  19. washeluted with 70% EtOAc in hexanes

Sources & evidence

ORD record
ord-bd2b2f269baf40448b5acb336d42165e
Source dataset
uspto-grants-2015_03
Patent number
US08987435B2

Reaction notes

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