Diisopropylethylamine → Benzyl {2-[((3S)-3-{[(benzyloxy)carbonyl]amino}-6-{[N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithyl]amino}hexanoyl)amino]ethyl}carbamate

HRID 269632ノート

反応式

HRID 269632 の反応式
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25](N(CC)C(C)C)(C)[CH3:26].[CH2:34]([O:41][C:42]([NH:44][CH2:45][CH2:46][CH2:47][C@@H:48]([C:57]([OH:59])=O)[NH:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl.C([N:68]([C@H:72]([CH2:77][C:78]([NH:80][CH2:81][CH2:82][NH:83][C:84]([O:86][CH2:87][C:88]1[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1)=[O:85])=[O:79])[CH2:73][CH2:74][CH2:75][NH2:76])[C:69](=[O:71])[OH:70])C1C=CC=CC=1>CN(C=O)C>[CH2:87]([O:86][C:84](=[O:85])[NH:83][CH2:82][CH2:81][NH:80][C:78](=[O:79])[CH2:77][C@@H:72]([NH:68][C:69]([O:70][CH2:10][C:11]1[CH:26]=[CH:25][CH:14]=[CH:13][CH:12]=1)=[O:71])[CH2:73][CH2:74][CH2:75][NH:76][C:57](=[O:59])[C@H:48]([CH2:47][CH2:46][CH2:45][NH:44][C:42]([O:41][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:43])[NH:49][C:50]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:51])[C:88]1[CH:89]=[CH:90][CH:91]=[CH:92][CH:93]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 7269338(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69216382benzyl((1S)-4-amino-1-{2-[(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-2-oxoethyl}butyl)carbamate hydrochloride

生成物 1

HCID 86624503Benzyl {2-[((3S)-3-{[(benzyloxy)carbonyl]amino}-6-{[N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithyl]amino}hexanoyl)amino]ethyl}carbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

89.5 mg (0.235 mmol) of HATU and 55.3 mg (0.428 mmol) of N,N-diisopropylethylamine are added to a solution of 78.4 mg (0.214 mmol) of N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithine in 5 ml of anhydrous DMF. After stirring at RT for 15 min, a solution of 116 mg (0.235 mmol) of benzyl((1S)-4-amino-1-{2-[(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-2-oxoethyl}butyl)carbamate hydrochloride (Example 105A) in 5 ml of anhydrous DMF is added. The reaction mixture is stirred at RT for 15 h. The solvent is then evaporated and the residue is taken up in dichloromethane. The organic phase is washed with water, dried over magnesium sulfate and concentrated. The crude product is purified by preparative HPLC.

後処理

  1. stirringThe reaction mixture is stirred at RT for 15 h
  2. customThe solvent is then evaporated
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative HPLC

出典と根拠

ORDレコード
ord-26c96ae642404579bb6d0beb581adc2f
出典データセット
uspto-grants-2008_11
特許番号
US07446102B2

反応ノート

読み込み中…