Diisopropylethylamine → {(3S,5S)-1-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetyl)-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 1481912노트

반응식

HRID 1481912 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O.[CH:59]1[C:71]2[CH:70]([CH2:72][O:73][C:74](=[O:94])[NH:75][C@H:76]3[CH2:80][C@@H:79]([C:81](=[O:93])[NH:82][C@H:83]4[C:92]5[C:87](=[CH:88][CH:89]=[CH:90][CH:91]=5)[CH2:86][CH2:85][CH2:84]4)[NH:78][CH2:77]3)[C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[C:63]=2[CH:62]=[CH:61][CH:60]=1>CN(C=O)C>[CH:68]1[C:69]2[CH:70]([CH2:72][O:73][C:74](=[O:94])[NH:75][C@H:76]3[CH2:80][C@@H:79]([C:81](=[O:93])[NH:82][C@H:83]4[C:92]5[C:87](=[CH:88][CH:89]=[CH:90][CH:91]=5)[CH2:86][CH2:85][CH2:84]4)[N:78]([C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:13]4[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)[CH2:77]3)[C:71]3[C:63](=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:64]=2[CH:65]=[CH:66][CH:67]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 7004938N-(tert-Butoxycarbonyl)-L-cyclohexylglycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90220816{(3S,5S)-5-[(R)-(1,2,3,4-Tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester trifluoroacetate2회

생성물 1

HCID 90220880{(3S,5S)-1-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetyl)-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of (S)-tert-butoxycarbonylamino-cyclohexyl-acetic acid (Aldrich) (4.529 g, 17.622 mmol) in DMF (100 mL) were added HATU (6.7 g, 17.622 mmol) followed by DIPEA (13.87 mL, 80.101 mmol). The mixture was cooled to 0° C. and ({(3S,5S)-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester trifluoroacetate (Intermediate 22) (9.5 g, 16.02 mmol) in DMF (50 mL) was added dropwise and then the cooling bath removed. After 4 h the mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated to give the title compound as an off white solid (10 g) which was used without purification. LC-MS: 721 (M+H).

후처리

  1. customthe cooling bath removed
  2. additionAfter 4 h the mixture was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-21a17a61a9ef420086a2d45e0d3748bf
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409888B2

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