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Diisopropylethylamine → {(3S,5S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-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 1481914
ノート
印刷プレビュー

反応式

HRID 1481914 の反応式
[N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:7])[C@H:2]([C:4]([OH:6])=O)[CH3:3].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.[CH:48]1[C:60]2[CH:59]([CH2:61][O:62][C:63](=[O:93])[NH:64][C@H:65]3[CH2:69][C@@H:68]([C:70](=[O:82])[NH:71][C@H:72]4[C:81]5[C:76](=[CH:77][CH:78]=[CH:79][CH:80]=5)[CH2:75][CH2:74][CH2:73]4)[N:67]([C:83](=[O:92])[C@@H:84]([NH2:91])[CH:85]4[CH2:90][CH2:89][CH2:88][CH2:87][CH2:86]4)[CH2:66]3)[C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[C:52]=2[CH:51]=[CH:50][CH:49]=1>CN(C=O)C.C(OCC)(=O)C>[CH:48]1[C:60]2[CH:59]([CH2:61][O:62][C:63](=[O:93])[NH:64][C@H:65]3[CH2:69][C@@H:68]([C:70](=[O:82])[NH:71][C@H:72]4[C:81]5[C:76](=[CH:77][CH:78]=[CH:79][CH:80]=5)[CH2:75][CH2:74][CH2:73]4)[N:67]([C:83](=[O:92])[C@@H:84]([NH:91][C:4](=[O:6])[C@@H:2]([N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:7])[CH3:3])[CH:85]4[CH2:90][CH2:89][CH2:88][CH2:87][CH2:86]4)[CH2:66]3)[C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[C:52]=2[CH:51]=[CH:50][CH:49]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118677380{(3S,5S)-1-((S)-2-amino-2-cyclohexyl-acetyl)-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester2 回

生成物 1

HCID 90220982
{(3S,5S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-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 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of Boc-N-Me-Ala-OH (2.55 g, 12.57 mmol) in DMF (30 mL) were added HATU (4.78 g, 12.57 mmol) and DIPEA (9.9 mL, 57.16 mmol). After 30 min, the mixture was cooled to 0° C. and {(3S,5S)-1-((S)-2-amino-2-cyclohexyl-acetyl)-5-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-3-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester (Intermediate 24) (7.5 g, 11.43 mmol) in DMF (50 mL) and the cooling bath removed. After 4 h the mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography to afford the title compound as an off white solid (5.32 g) LC-MS: 806 (M+H).

後処理

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-7436cab788b74d768e44b9ad011b6e48
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409888B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート