Dichloromethane → HCID 178454250, compound

HRID 708412Notes

Reaction equation

HRID 708412 reaction equation
FC(F)(F)[C:3]([O-:5])=[O:4].[NH3+:8][CH2:9][C:10]1[N:11]=[N:12][N:13]([CH2:15][C@@H:16]2[C@H:19]([NH:20][C:21](=[O:37])/[C:22](=[N:29]\[O:30][C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=[O:33])/[C:23]3[N:24]=[C:25]([NH2:28])[S:26][CH:27]=3)[C:18](=[O:38])[N:17]2[S:39]([OH:42])(=[O:41])=[O:40])[CH:14]=1.CCN([CH:49]([CH3:51])[CH3:50])C(C)C.[C:52]([N:59](C(OC(C)(C)C)=O)[C:60](N1C=CC=N1)=[NH:61])([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53].[CH2:74](Cl)Cl>>[NH2:28][C:25]1[S:26][CH:27]=[C:23](/[C:22](=[N:29]/[O:30][C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=[O:33])/[C:21]([NH:20][C@@H:19]2[C:18](=[O:38])[N:17]([S:39]([OH:42])(=[O:41])=[O:40])[C@@H:16]2[CH2:15][N:13]2[CH:14]=[C:10]([CH2:9][NH:8][C:60]([NH:59][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[N:61][C:3]([O:5][C:49]([CH3:51])([CH3:74])[CH3:50])=[O:4])[N:11]=[N:12]2)=[O:37])[N:24]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 22592956HCID 22592956, compoundHCID 118380121HCID 118380121, compound

Product 1

HCID 178454250HCID 178454250, compound

Procedure

To a solution of 2-(((Z)-(2-(((2R,3S)-2-((4-(ammoniomethyl)-1H-1,2,3-triazol-1-yl)methyl)-4-oxo-1-sulfoazetidin-3-yl)amino)-1-(2-aminothiazol-4-yl)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate (150 mg, 0.122 mmol) In DCM (10 mL) was added DIPEA (100 μL, 0.610 mmol) followed N,N-di-Boc-1H-pyrazole-1-carboxamidine (42 mg, 0.134 mmol). The solution was stirred at RT overnight whereupon it was concentrated in vacuo, water was added and it was lyophilized for 72 h to afford crude title compound (210 mg, assumed quantitative conversion). LCMS: m/z=772.1 (M−1).

Workup

  1. concentrationwas concentrated in vacuo, water
  2. additionwas added
  3. waitit was lyophilized for 72 h

Sources & evidence

ORD record
ord-901a506394df405aa88a67d43fd5c24c
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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