Diisopropylethylamine → HCID 118379722, compound

HRID 708551Notes

Reaction equation

HRID 708551 reaction equation
[CH:1]([O:14][C:15]([C:17]1([O:20]/[N:21]=[C:22](/[C:26]2[N:27]=[C:28]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[S:29][CH:30]=2)\[C:23](O)=[O:24])[CH2:19][CH2:18]1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:72][C@@H:73]1[C:76](=[O:77])[NH:75][C@@H:74]1[CH2:78][N:79]1[N:83]=[C:82]([C@@H:84]([NH:95][C:96](=[O:102])[O:97][C:98]([CH3:101])([CH3:100])[CH3:99])[CH2:85][CH2:86][NH:87][C:88](=[O:94])[O:89][C:90]([CH3:93])([CH3:92])[CH3:91])[CH:81]=[N:80]1>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[C:35]([O:34][C:32]([NH:31][C:28]1[S:29][CH:30]=[C:26](/[C:22](=[N:21]/[O:20][C:17]2([C:15]([O:14][CH:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:16])[CH2:18][CH2:19]2)/[C:23](=[O:24])[NH:72][C@H:73]2[C@@H:74]([CH2:78][N:79]3[N:83]=[C:82]([C@H:84]([CH2:85][CH2:86][NH:87][C:88](=[O:94])[O:89][C:90]([CH3:93])([CH3:91])[CH3:92])[NH:95][C:96](=[O:102])[O:97][C:98]([CH3:101])([CH3:100])[CH3:99])[CH:81]=[N:80]3)[NH:75][C:76]2=[O:77])[N:27]=1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

7

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 118380020(Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acidHCID 131733859HCID 131733859, compound

Product 1

HCID 118379722HCID 118379722, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid (582 mg, 1.028 mmol), DIPEA (0.269 mL, 1.543 mmol) and HATU (430 mg, 1.131 mmol) in DCM/DMF (12 mL, 5:1) was stirred at 0° C. for 30 min. To this mixture was added di-tert-butyl ((S)-1-(2-(((2R,3S)-3-amino-4-oxoazetidin-2-yl)methyl)-2H-1,2,3-triazol-4-yl)propane-1,3-diyl)dicarbamate (1.03 mmol). After stirring for an additional 30 min at 0° C., it was diluted with EtOAc, washed with water, brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified via silica gel chromatography (EtOAc-Heptane) to afford the title compound (760 mg, 77%). LCMS: Rt=1.12 min, m/z=959.6 (M+1) Method 2m_acidic.

Workup

  1. stirringAfter stirring for an additional 30 min at 0° C.
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified via silica gel chromatography (EtOAc-Heptane)

Sources & evidence

ORD record
ord-6be74cc3e4844e6da72b4689f7f50bde
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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