Reaction equation
CCN(C(C)C)C(C)C.[CH3:10][C:11]([O:14][C:15]([NH:17][C@H:18]([C:27]([OH:29])=O)[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:16])([CH3:13])[CH3:12].[NH2:30][C@H:31]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[CH2:32][CH:33]([CH3:35])[CH3:34].CC1C=CC(S(O)(=O)=O)=CC=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>C(Cl)Cl>[C:11]([O:14][C:15]([NH:17][C@@H:18]([CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:27]([NH:30][C@@H:31]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])=[O:29])=[O:16])([CH3:10])([CH3:12])[CH3:13]Participants
8
Reactant 6
HCID 313Hydrochloric Acid
HCID 6101p-Toluenesulfonic acid
HCID 81531Diisopropylethylamine
HCID 6451313Benzyl L-leucinate
HCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)Product 1
Reagents, catalysts & solvents 1
Procedure
Referring to FIG. 45, DIPEA (2 mL, 12 mmol, 2.7 eq) was added to a mixture of Boc-HoPhe-OH (1.25 g, 4.4 mmol, 1 eq). H-Leu-OBn.TsOH (1.75 g, 4.5 mmol, 1.0 eq) and HATU (2 g, 5 mmol, 1.1 eq) in CH2Cl2 (50 mL) and the mixture was stirred for four hours at RT. The mixture was poured into 0.5N aq. HCl and extracted twice with CH2Cl2. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (SiO2, 0-30% EtOAc in heptanes) and product (2.7 g, 100%) was isolated as a colorless oil.
Workup
- extractionextracted twice with CH2Cl2
- dry with materialThe combined organic extracts were dried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography (SiO2, 0-30% EtOAc in heptanes)
Sources & evidence
- ORD record
- ord-66bf90c18381461b8ec7fc4f78c1ccf0
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315542B2
Linked notes
Loading…