Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 87237095, compound

HRID 1617775Notes

Reaction equation

HRID 1617775 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9](=O)[CH2:10][CH:11]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:3]1.[NH2:29][CH2:30][C@@H:31]([OH:33])[CH3:32].CN([P+]([O:44][N:45]1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.Cl.NO.C([O-])(O)=O.[Na+]>O1CCCC1>[OH:44]/[N:45]=[C:9](/[C:4]1[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[CH:3]=1)\[CH2:10][CH:11]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:29][CH2:30][C@H:31]([OH:33])[CH3:32])=[O:24])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Participants

7

Reactant 5

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 670155254-[3-(1-Methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid

Product 1

HCID 87237095HCID 87237095, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to example 207, step 2, 4-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid (example 207, step 1) was coupled with (S)-(+)-1-amino-2-propanol using BOP reagent in tetrahydrofuran. The product of this reaction was reacted in analogy to example 151, step 3, with hydroxylamine hydrochloride in the presence of NaHCO3 to give the title compound containing 5% of the corresponding Z isomer as a colorless solid, MS (ESI+): m/z=448.2 [M+H]+.

Sources & evidence

ORD record
ord-5c548794014943c39483421c9f121188
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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