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Triethylamine → HCID 57687746, 화합물

HRID 1880819
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HRID 1880819 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:7][OH:8].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(N(CC)CC)C.[CH3:59][O:60][C:61]([NH:63][C@@H:64]([CH:68]([C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:65](O)=[O:66])=[O:62]>C(Cl)Cl>[CH3:59][O:60][C:61](=[O:62])[NH:63][C@H:64]([C:65](=[O:66])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([S:10]([C:13]1[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=1)(=[O:12])=[O:11])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:7][OH:8])[CH:68]([C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acidHCID 67530865HCID 67530865, 화합물

생성물 1

HCID 57687746HCID 57687746, 화합물수율 84%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

(S)—N-(5-Amino-1-hydroxymethyl-pentyl)-4-cyano-N-isobutyl-benzenesulfonamide (6) obtained in the previous reaction was dissolved in 50 mL CH2Cl2. BOP (1.2 eq), and triethylamine (5 eq) were added. After 10 minutes, (S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid (1 eq) was added and the mixture was stirred at RT for 3 hours. LCMS indicated a complete reaction. The reaction mixture was washed with sat. NaHCO3. The aqueous phase was washed again with 100 mL CH2Cl2. The combined organic layers where dried with MgSO4, filtered over dicalite and evaporated to dryness. The residue was purified by column chromatography with CH2Cl2-MeOH(NH3) (97:3). The appropriate fraction was evaporated to dryness. (1.31 g, 84% yield over 2 steps)

후처리

  1. customa complete reaction
  2. washThe reaction mixture was washed with sat. NaHCO3
  3. washThe aqueous phase was washed again with 100 mL CH2Cl2
  4. dry with materialThe combined organic layers where dried with MgSO4
  5. filtrationfiltered over dicalite
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography with CH2Cl2-MeOH(NH3) (97:3)
  8. customThe appropriate fraction was evaporated to dryness

출처 및 근거

ORD 기록
ord-31b13a880c4f4c4193747ff301fcfcd8
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318779B2

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