Formic Acid → HCID 90387472, compound

HRID 508402Notes

Reaction equation

HRID 508402 reaction equation
[CH:1](O)=[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.[NH2:37][C@H:38]([CH2:47][C:48]1[CH:53]=[CH:52][C:51]([C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([Cl:60])[CH:55]=2)=[CH:50][CH:49]=1)[CH2:39][C@:40]([CH2:45][OH:46])([CH3:44])[C:41]([OH:43])=[O:42]>CN(C=O)C>[Cl:60][C:56]1[CH:55]=[C:54]([C:51]2[CH:52]=[CH:53][C:48]([CH2:47][C@@H:38]([NH:37][CH:1]=[O:2])[CH2:39][C@:40]([CH2:45][OH:46])([CH3:44])[C:41]([OH:43])=[O:42])=[CH:49][CH:50]=2)[CH:59]=[CH:58][CH:57]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 81531Diisopropylethylamine2×HCID 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 90387472HCID 90387472, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Formic acid (3 mg, 32 μmol) was combined with HATU (12 mg, 32 μmol) and DMF (0.2 mL) and stirred for 5 minutes. DIPEA (17 μl, 96 μmol) was added, followed by (2S,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxymethyl-2-methyl-pentanoic acid (79 mg, 38 μmol) pre-dissolved in DMF (0.5 mL) and DIPEA (17 μl, 96 μmol). The resulting mixture was stirred for 15 minutes. The solvent was removed in vacuo and the residue was dissolved in AcOH and purified by preparative HPLC to yield the title compound (0.5 mg). MS m/z [M+H]+ calc'd for C20H22ClNO4, 376.12. found 376.2.

Workup

  1. stirringThe resulting mixture was stirred for 15 minutes
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in AcOH
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-ee8033c3377c4efe939b4c0cd7822a7d
Source dataset
uspto-grants-2015_08
Patent number
US09096496B2

Reaction notes

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