Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 22877901, compound

HRID 1488861Notes

Reaction equation

HRID 1488861 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C[N:28]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH:54]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C@H:55]([C:59](O)=[O:60])[C@@H:56]([CH3:58])[OH:57].C(=O)([O-])O.[Na+]>C(#N)C.O.C(N(CC)CC)C>[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:62]([NH:54][C@H:55]([C:59]([NH2:28])=[O:60])[C@@H:56]([CH3:58])[OH:57])([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63]

Participants

8

Reactant 4

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 2724766N-tert-Butoxycarbonyl-L-threonineHCID 9976854HCID 9976854, compound

Product 1

HCID 22877901HCID 22877901, compoundYield 55.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

One-thousand milligrams (2.65 mmols) of (E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride, 1,300 mg of a BOP reagent and 880 mg of Boc-L-Thr (OtBu) were dissolved in 50 ml of acetonitrile, and 0.8 ml of triethylamine were added thereto. The mixture was reacted at 60° C. for 21 hours. One-hundred milliliters of water and a small amount of sodium hydrogencarbonate were added thereto, and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The product was purified using a silica-gel column (eluent, mixture of ethyl acetate and hexane at a ratio by volume of 5:1), and then concentrated to produce 870 mg (1.46 mmols) of the final product in a yield of 55%.

Workup

  1. customThe mixture was reacted at 60° C. for 21 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified
  7. additioneluent, mixture of ethyl acetate and hexane at a ratio by volume of 5:1), and
  8. concentrationthen concentrated

Sources & evidence

ORD record
ord-fbdc33db9df848a2a975dfc63701b934
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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