N,N-dimethylhydroxylamine hydrochloride → HCID 90120002, compound

HRID 2202546Notes

Reaction equation

HRID 2202546 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([C:31]([O:35][N:36]1N=NC2C=CC=C[C:37]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CN(C)O>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:13]([N:36]([O:35][CH3:31])[CH3:37])=[O:15])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7408150HCID 7408150, compound

Product 1

HCID 90120002HCID 90120002, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-2-(((benzyloxy)carbonyl)amino)-8-(tert-butoxy)-8-oxooctanoic acid (prepared as described in WO2006/061638), HBTU (1.1 eq.) and DIPEA (2 eq.) in DMF (0.7 M) was stirred at room temperature for 10 min. Then, dimethylhydroxylamine hydrochloride (1.1 eq.) was added. The reaction mixture was stirred at room temperature for a further 16 h then diluted with EtOAc. Organic phase was washed with sat. aq. NaHCO3, brine, dried over Na2SO4 and concentrated under reduced pressure to give a residue that was purified by column chromatography (eluent: petroleum ether/EtOAc from 85:15 to 1:4) to give the title compound as a pale yellow oil. MS (ES+) C22H34N2O6: 423 (M+H)+.

Workup

  1. washOrganic phase was washed with sat. aq. NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue that
  5. customwas purified by column chromatography (eluent: petroleum ether/EtOAc from 85:15 to 1:4)

Sources & evidence

ORD record
ord-099a306256374cf3a04ec3e66e02e406
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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