Diisopropylethylamine → 9h-fluoren-9-ylmethyl{(1S)-4-amino-1-[({(2s)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-oxobutyl}carbamate

HRID 269650Notes

Reaction equation

HRID 269650 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH:34]1[C:46]2[CH:45]([CH2:47][O:48][C:49]([NH:51][C@H:52]([C:58](O)=[O:59])[CH2:53][CH2:54][C:55](=[O:57])[NH2:56])=[O:50])[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1.[C:61]([O:65][C:66](=[O:82])[NH:67][CH2:68][CH2:69][CH2:70][C@H:71]([NH:74][C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[CH2:72][NH2:73])([CH3:64])([CH3:63])[CH3:62]>CN(C=O)C>[CH:43]1[C:44]2[CH:45]([CH2:47][O:48][C:49](=[O:50])[NH:51][C@H:52]([C:58]([NH:73][CH2:72][C@@H:71]([NH:74][C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[CH2:70][CH2:69][CH2:68][NH:67][C:66]([O:65][C:61]([CH3:63])([CH3:64])[CH3:62])=[O:82])=[O:59])[CH2:53][CH2:54][C:55]([NH2:56])=[O:57])[C:46]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:39]=2[CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724775N2-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-glutamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57440197tert-Butyl {(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

Product 1

HCID 708066899h-fluoren-9-ylmethyl{(1S)-4-amino-1-[({(2s)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-oxobutyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

129 mg (0.34 mmol) of HATU and 133 mg (0.95 mmol) of N,N-diisopropylethylamine are added to a solution of 100 mg (0.27 mmol) of N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine and 112 mg (0.35 mmol) of tert-butyl{(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate (Example 86A) in 5 ml of anhydrous DMF at 0° C. The reaction mixture is stirred at RT for 15 h. The solvent is then evaporated and the residue is stirred with water, collected by filtration and dried under high vacuum.

Workup

  1. customThe solvent is then evaporated
  2. stirringthe residue is stirred with water
  3. filtrationcollected by filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-81743811b6c4430b81ef7e79aebcb1cc
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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