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

HRID 1488861노트

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HRID 1488861 반응식
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]

참가 물질

8

반응물 4

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 2724766N-tert-Butoxycarbonyl-L-threonineHCID 9976854(E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride

생성물 1

HCID 22877901HCID 22877901, 화합물수율 55.1%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-fbdc33db9df848a2a975dfc63701b934
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05674906

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