Diisopropylethylamine → HCID 86680332, compound

HRID 2279176Notes

Reaction equation

HRID 2279176 reaction equation
[C:1]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].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.[CH3:47][O:48][C:49](=[O:63])[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>[CH3:47][O:48][C:49](=[O:63])[C@H:50]([N:53]([C:11](=[O:13])[C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:10])[CH2:54][C:55]1[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=1)[CH2:51][CH3:52]

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 85082Tert-butoxycarbonylalanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 86680330(R)-2-(4-Methoxy-benzylamino)-butyric acid methyl ester

Product 1

HCID 86680332HCID 86680332, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

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 reation 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 wer washed with 10% aqueous citric acid twice, dried over Na2SO4, fitrered 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

  1. stirringthe reaction was stirred for 24 h at r.t.
  2. waitfor 4 h at 50° C
  3. customthe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc twice
  5. washThe combined organic layers wer washed with 10% aqueous citric acid twice
  6. dry with materialdried over Na2SO4
  7. concentrationfitrered and concentrated in vacuo
  8. customThe residue was purified by flash chromatography (silica, heptane/EtOAc)

Sources & evidence

ORD record
ord-500590863c5d45da841bf37afcd33944
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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