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

HRID 269632노트

반응식

HRID 269632 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-26c96ae642404579bb6d0beb581adc2f
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446102B2

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