1-Hydroxybenzotriazole → HCID 22877902, compound

HRID 1488864Notes

Reaction equation

HRID 1488864 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].[NH:27]([C:38]([O:40][CH2:41][CH:42]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:48]2[C:43]1=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:39])[C@H:28]([C:35](O)=[O:36])[CH2:29][O:30]C(C)(C)C.C[N:56]([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>[NH2:2][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:38]([NH:27][C@H:28]([C:35]([NH2:56])=[O:36])[CH2:29][OH:30])([O:40][CH2:41][CH:42]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:48]2[C:43]1=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:39]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 2724633N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylserineHCID 9976854HCID 9976854, compound

Product 1

HCID 22877902HCID 22877902, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride (1,007 mg, 2.65 mmols), 1,105 mg of Fmoc-L-Ser(OtBu)OH, 1,370 mg of a BOP reagent and 618 mg of HOBt.H2O were dissolved in 50 ml of acetonitrile, and 0.8 ml of triethylamine were added thereto. The mixture was reacted at 60° C. for 42 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 of 2:3), and then concentrated to produce 1,486 mg (2.14 mmols) of the final product in a yield of 81%.

Workup

  1. customThe mixture was reacted at 60° C. for 42 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 of 2:3), and
  8. concentrationthen concentrated

Sources & evidence

ORD record
ord-336f4b24cb8344ffb7d8c0c14e9837ca
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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