Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 22877914, compound

HRID 1488848Notes

Reaction equation

HRID 1488848 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]\[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[NH:24]([C:30]([O:32][CH2:33][CH:34]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C@H:25]([C:27](O)=[O:28])[CH3:26].C[N:48]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]\[C:12]2[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:30]([NH:24][C@H:25]([C:27]([NH2:48])=[O:28])[CH3:26])([O:32][CH2:33][CH:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]2[C:46]1=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:31]

Participants

6

Reactant 4

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 6364642N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanineHCID 9796936AC-7739 free base

Product 1

HCID 22877914HCID 22877914, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(Z)-1-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-ethene (2.2 g, 6.9 mmols), 2.7 g (8.3 mmols) of Fmoc-L-Ala and 12.1 g (27.6 mmols) of a BOP reagent were dissolved in 22 ml of N,N-dimethylformamide, and the mixture was heated at 60° C. for 4 hours. After the reaction mixture was cooled, a saturated aqueous solution of sodium hydrogencarbonate was added thereto, and the resulting mixture was extracted three times with dichloromethane. The extract was dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The product was purified through silica-gel column chromatography (mixture of ethyl acetate and hexane at a ratio of 1:2) to produce 1.79 g of the final product in a yield of 41.4%.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. extractionthe resulting mixture was extracted three times with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe product was purified through silica-gel column chromatography (
  6. additionmixture of ethyl acetate and hexane at a ratio of 1:2)

Sources & evidence

ORD record
ord-dd07457074c04c1b99d4ae14bde1cd3d
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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