Diisopropylethylamine → HCID 89964063, compound

HRID 2275497Notes

Reaction equation

HRID 2275497 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[C:6]([C:8]([OH:10])=O)[O:5][N:4]=1.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.[NH2:44][C@H:45]([CH2:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[CH:66]=[CH:65][CH:64]=[C:63]([Cl:67])[CH:62]=2)=[CH:57][CH:56]=1)[CH2:46][C@:47]([CH2:52][OH:53])([CH3:51])[C:48]([OH:50])=[O:49]>CN(C=O)C>[Cl:67][C:63]1[CH:62]=[C:61]([C:58]2[CH:57]=[CH:56][C:55]([CH2:54][C@@H:45]([NH:44][C:8]([C:6]3[O:5][N:4]=[C:3]([O:2][CH3:1])[CH:7]=3)=[O:10])[CH2:46][C@:47]([CH2:52][OH:53])([CH3:51])[C:48]([OH:50])=[O:49])=[CH:60][CH:59]=2)[CH:66]=[CH:65][CH:64]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3277173-Methoxy-1,2-oxazole-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89964569HCID 89964569, compound

Product 1

HCID 89964063HCID 89964063, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Methoxyisoxazole-5-carboxylic acid (9 mg, 32 μmol) was combined with HATU (12 mg, 32 μmol) and DMF (0.2 mL) and the resulting mixture was stirred for 5 minutes. DIPEA (17 μL, 96 μmol) and (2S,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxymethyl-2-methylpentanoic acid (79 mg, 38 μmol) pre-dissolved in DMF were added and the resulting mixture was stirred for 15 minutes then concentrated. The residue was dissolved in AcOH and purified by preparative HPLC to yield the title compound (2.2 mg). MS m/z [M+H]+ calc'd for C24H25ClN2O6, 473.14. found 473.2.

Workup

  1. additionwere added
  2. stirringthe resulting mixture was stirred for 15 minutes
  3. concentrationthen concentrated
  4. dissolutionThe residue was dissolved in AcOH
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-aeb65247eb694c4b87f939ff4e5a6493
Source dataset
uspto-grants-2015_09
Patent number
US09126956B2

Reaction notes

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