Hydroxyamine hydrochloride → HCID 136385669, compound

HRID 1617529Notes

Reaction equation

HRID 1617529 reaction equation
CC1C=C(C(=O)C[C@H](C2C=CC(C3C=CC(C(NCC(O)=O)=O)=CC=3)=CC=2)C2C=CC=CC=2C)C=CN=1.Cl.NO.C([O-])(O)=O.[Na+].[OH:46][N:47]=[C:48]([C:77]1[CH:82]=[CH:81][N:80]=[C:79]([CH3:83])[CH:78]=1)[CH2:49][C@H:50]([C:58]1[CH:63]=[CH:62][C:61]([C:64]2[CH:69]=[CH:68][C:67]([C:70]([NH:72][CH2:73][C:74]([OH:76])=[O:75])=[O:71])=[CH:66][CH:65]=2)=[CH:60][CH:59]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[CH3:57]>>[OH:46]/[N:47]=[C:48](/[C:77]1[CH:82]=[CH:81][N:80]=[C:79]([CH3:83])[CH:78]=1)\[CH2:49][C@H:50]([C:58]1[CH:59]=[CH:60][C:61]([C:64]2[CH:69]=[CH:68][C:67]([C:70]([NH:72][CH2:73][C:74]([OH:76])=[O:75])=[O:71])=[CH:66][CH:65]=2)=[CH:62][CH:63]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[CH3:57]

Participants

5

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 66666832HCID 66666832, compoundHCID 136359996HCID 136359996, compound

Product 1

HCID 136385669HCID 136385669, compound

Procedure

In analogy to example 74, step 7, from ({4′-[(R)-3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carbonyl}-amino)-acetic acid and hydroxylamine hydrochloride in the presence of NaHCO3 was prepared ({4′-[(R)-3-[hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carbonyl}-amino)-acetic acid as a mixture of isomers which was separated by chiral HPLC (Reprosil-Chiral-NR, 70% n-heptane, 30% ethanol+0.5% formic acid) to give the title compound as a white solid, MS (ESI+): m/z=508.3 ([M+H]+).

Workup

  1. additionas a mixture of isomers which
  2. customwas separated by chiral HPLC (Reprosil-Chiral-NR, 70% n-heptane, 30% ethanol+0.5% formic acid)

Sources & evidence

ORD record
ord-89a28c33ccf14a23a728a6e0a73b17f4
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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