Triethylamine → 4-[3-(Pyridin-4-yl)propyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine

HRID 265885노트

반응식

HRID 265885 반응식
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[CH:3][CH:2]=1.CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:54]1([S:60]([NH:63][C@@H:64]([CH2:68][NH2:69])[C:65]([OH:67])=[O:66])(=[O:62])=[O:61])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>CN(C=O)C>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:69][CH2:68][C@H:64]([NH:63][S:60]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)(=[O:62])=[O:61])[C:65]([OH:67])=[O:66])=[O:17])=[CH:18][CH:19]=2)=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10752796(2S)-3-amino-2-(benzenesulfonamido)propanoic AcidHCID 190341454-[3-(Pyridin-4-yl)propyloxy]benzoic acid

생성물 1

HCID 104579924-[3-(Pyridin-4-yl)propyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine수율 106.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 19-5 (200 mg, 0.78 mmol), NEt3 (0.22 mL, 1.5 mmol), and DMF (4 mL) at ambient temperature was treated with BOP (345 mg, 0.78 mmol). After 3.0 h, NEt3 (0.22 mL, 1.5 mmol) and 19-2 (190 mg, 0.78 mmol) were added. After 20 h, the reaction mixture was concentrated and subjected to flash chromatography (silica, 10/1/1 CH2Cl2 /CH3OH/AcOH) to give impure 19-6 (400 mg). Prep HPLC purification (Delta Pak C-18Å column, 0 to 100% CH3CN/H2O containing 0.1% trifluoroacetic acid) gave pure 19-6 as a whim solid after lyophilization. Rf 0.74 (silica, 10/1/1 CH2Cl2 /CH3OH/AcOH).

후처리

  1. waitAfter 20 h
  2. concentrationthe reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-9a3be4b102b74f0a80c4affd98609cfc
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648368

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