Diisopropylethylamine → HCID 73053060, compound

HRID 2275496Notes

Reaction equation

HRID 2275496 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]=[C:4]([C:7]([OH:9])=O)[O:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:34][C@H:35]([CH2:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:56]=[C:55]([Cl:57])[CH:54]=[CH:53][C:52]=2[F:58])=[CH:47][CH:46]=1)[CH2:36][C@:37]([CH2:42][OH:43])([CH3:41])[C:38]([OH:40])=[O:39].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:57][C:55]1[CH:54]=[CH:53][C:52]([F:58])=[C:51]([C:48]2[CH:47]=[CH:46][C:45]([CH2:44][C@@H:35]([NH:34][C:7]([C:4]3[O:3][C:2](=[O:1])[NH:6][CH:5]=3)=[O:9])[CH2:36][C@:37]([CH2:42][OH:43])([CH3:41])[C:38]([OH:40])=[O:39])=[CH:50][CH:49]=2)[CH:56]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 539814232-Hydroxy-1,3-oxazole-5-carboxylic acidHCID 89964351HCID 89964351, compound

Product 1

HCID 73053060HCID 73053060, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Oxo-2,3-dihydrooxazole-5-carboxylic acid (7.1 mg, 55 μmol) and HATU (21 mg, 55 μmol) were combined in DMF (0.3 mL) and stirred at room temperature for 5 minutes. (2S,4R)-4-Amino-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-hydroxymethyl-2-methylpentanoic acid (20 mg, 55 μmol) in DMF (0.5 mL) and DIPEA (29 μL, 164 μmol) were added, and the resulting mixture was stirred for 10 minutes at room temperature. The mixture was concentrated under reduced pressure and the residue was dissolved in AcOH purified by preparative HPLC to yield the title compound (3 mg). MS m/z [M+H]+ calc'd for C23H22ClFN2O6, 477.12. found 477.

Workup

  1. stirringthe resulting mixture was stirred for 10 minutes at room temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in AcOH
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-10941a0ca6c7409d8e18ff8071ca324a
Source dataset
uspto-grants-2015_09
Patent number
US09126956B2

Reaction notes

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