1-Hydroxybenzotriazole → HCID 178490140, compound

HRID 1488866Notes

Reaction equation

HRID 1488866 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[C:11](\[C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)/[C:12]#[N:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[NH:26]([C:42]([O:44]CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=[O:43])[C@H:27]([C:39](O)=[O:40])[CH2:28][C:29](=[O:38])[O:30]CC1C=CC=CC=1.C[N:60]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])O.[Na+]>C(#N)C.O.C(N(CC)CC)C>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[C:11](\[C:14]2[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)/[C:12]#[N:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:42]([NH:26][C@H:27]([C:39]([NH-:60])=[O:40])[CH2:28][C:29](=[O:38])[OH:30])([O:44][CH2:15][CH:16]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:2]=2)[C:10]2[C:17]1=[CH:18][CH:19]=[CH:14][CH:11]=2)=[O:43]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 9840884(E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrileHCID 13966931(2S)-4-(Benzyloxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-oxobutanoic acid

Product 1

HCID 178490140HCID 178490140, compoundYield 135.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Nine-hundred milligrams (2.65 mmols) of (E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile, 1,400 mg of Fmoc-L-Asp(OBn), 1,300 mg of a BOP reagent and 660 mg of HOBt.H2O were dissolved in 50 ml of acetonitrile, and 0.5 ml of triethylamine were added thereto. The mixture was reacted at room temperature for 86 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 dichloromethane at a ratio by volume of 1:10), and then concentrated to give 1,319 mg (1.80 mmols) of the final product in a yield of 68%.

Workup

  1. customThe mixture was reacted at room temperature for 86 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 dichloromethane at a ratio by volume of 1:10), and
  8. concentrationthen concentrated

Sources & evidence

ORD record
ord-9749be6281d0440ba596b352b549aafc
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

Loading…