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 1481912ノート

反応式

HRID 1481912 の反応式
[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

参加物

6

反応物 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 trifluoroacetate2 回

生成物 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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-21a17a61a9ef420086a2d45e0d3748bf
出典データセット
uspto-grants-2016_08
特許番号
US09409888B2

反応ノート

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