Diisopropylethylamine → HCID 86680329, compound
Reaction equation
C([NH:8][C@H:9]([C:11](O)=O)[CH3:10])(OC(C)(C)C)=O.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.CO[C:49](=O)[C@H:50]([NH:53][CH2:54][C:55]1[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=1)[CH2:51][CH3:52]>CN(C=O)C.O>[CH2:51]([C@@H:50]1[CH2:49][NH:8][C@@H:9]([CH3:11])[CH2:10][N:53]1[CH2:54][C:55]1[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=1)[CH3:52]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3.99 g of Boc-L-alanine in 50 ml of DMF were added 12.02 g of HATU, 4.3 ml of Hünig's base and 5.00 g (R)-2-(4-Methoxy-benzylamino)-butyric acid methyl ester. The reaction was stirred overnight, and 6.01 g of HATU and 2.1 ml of Hünig's base were added, and the reaction was stirred for 24 h at r.t. and then for 4 h at 50° C. The reaction was poured unto water, the layers were separated and the aqueous phase was extracted with EtOAc twice. The combined organic layers war washed with 10% aqueous citric acid twice, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/EtOAc) to obtain 7.60 g (88%) of the title compound.
Workup
- stirringthe reaction was stirred for 24 h at r.t.
- waitfor 4 h at 50° C
- customthe layers were separated
- extractionthe aqueous phase was extracted with EtOAc twice
- washThe combined organic layers war washed with 10% aqueous citric acid twice
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (silica, heptane/EtOAc)
Sources & evidence
- ORD record
- ord-98d900e33a76413f839c554af2849a07
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08686150B2
Reaction notes
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