Acetic Acid → HCID 178452993, compound

HRID 708438Notes

Reaction equation

HRID 708438 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=O)[C:15]([NH:17][C@H:18]2[C@@H:21]([CH2:22][N:23]3[CH2:27][CH2:26][O:25][C:24]3=[O:28])[N:20]([S:29]([OH:32])(=[O:31])=[O:30])[C:19]2=[O:33])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:35][O:36][C@H:37]([C:62]([O:64][CH:65]([C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)=[O:63])[CH2:38][O:39][C:40]1[CH:61]=[CH:60][C:43]([C:44](=[NH:59])[NH:45][CH:46]2[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][CH2:47]2)=[CH:42][CH:41]=1.CC(O)=O>C(Cl)(Cl)Cl.CCO>[CH:65]([O:64][C:62](=[O:63])[C@@H:37]([O:36]/[N:35]=[C:14](/[C:12]1[N:13]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[S:10][CH:11]=1)\[C:15]([NH:17][C@H:18]1[C@@H:21]([CH2:22][N:23]2[CH2:27][CH2:26][O:25][C:24]2=[O:28])[N:20]([S:29]([OH:32])(=[O:30])=[O:31])[C:19]1=[O:33])=[O:16])[CH2:38][O:39][C:40]1[CH:61]=[CH:60][C:43]([C:44](=[NH:59])[NH:45][CH:46]2[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:53])[CH2:48][CH2:47]2)=[CH:42][CH:41]=1)([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:72]1[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 118380247HCID 118380247, compound2×HCID 178452099HCID 178452099, compound

Product 1

HCID 178452993HCID 178452993, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6212ChloroformSolvent2×

Procedure

To a soln of (3S,4R)-3-(2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoacetamido)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidine-1-sulfonic acid (170 mg, 0.328 mmol) in CHCl3 (2 mL, ratio: 1) and EtOH (6 mL, ratio: 3) was added (S)-tert-butyl 4-(4-(2-(aminooxy)-3-(benzhydryloxy)-3-oxopropoxy)benzimidamido)piperidine-1-carboxylate (prepared according to WO2013110643, 193 mg, 0.328 mmol). After stirring for 2 h, AcOH (19 μL, 0.328 mmol) was added. After 12 h, more solution of (3S,4R)-3-(2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoacetamido)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidine-1-sulfonic acid (170 mg, 0.328 mmol) in 3:1 CHCl3:EtOH was added. After stirring for 45 h, it was concentrated in vacuo, and the crude residue was purified with HP21 resin (10-100% ACN-water), affording the title compound (117 mg, 33%) as an off white solid. LCMS: Rt=0.96 min, m/z=1091.1 (M+1) Method 2m_acidic.

Workup

  1. waitAfter 12 h
  2. stirringAfter stirring for 45 h
  3. concentrationit was concentrated in vacuo
  4. customthe crude residue was purified with HP21 resin (10-100% ACN-water)

Sources & evidence

ORD record
ord-b929a72a9e57415482b237bb86ba9f92
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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