Boron Trichloride → HCID 118379797, compound

HRID 708448Notes

Reaction equation

HRID 708448 reaction equation
C([O:8][CH2:9][C@@H:10]1[O:14][C:13](=[O:15])[N:12]([CH2:16][C@@H:17]2[C@H:20]([NH:21][C:22](=[O:49])/[C:23](=[N:37]\[O:38][C:39]([CH3:48])([CH3:47])[C:40]([O:42]C(C)(C)C)=[O:41])/[C:24]3[N:25]=[C:26]([NH:29]C(OC(C)(C)C)=O)[S:27][CH:28]=3)[C:19](=[O:50])[N:18]2[S:51]([OH:54])(=[O:53])=[O:52])[CH2:11]1)C1C=CC=CC=1.C(OC[C@@H]1OC(=O)N(C[C@@H]2[C@H](NC(=O)/C(=N\OC(C)(C)C(OC(C)(C)C)=O)/C3N=C(NC(OC(C)(C)C)=O)SC=3)C(=O)N2)C1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[NH2:29][C:26]1[S:27][CH:28]=[C:24](/[C:23](=[N:37]/[O:38][C:39]([CH3:48])([CH3:47])[C:40]([OH:42])=[O:41])/[C:22]([NH:21][C@@H:20]2[C:19](=[O:50])[N:18]([S:51]([OH:54])(=[O:53])=[O:52])[C@@H:17]2[CH2:16][N:12]2[CH2:11][C@H:10]([CH2:9][OH:8])[O:14][C:13]2=[O:15])=[O:49])[N:25]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 178452991HCID 178452991, compound

Product 1

HCID 118379797HCID 118379797, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(((Z)-(2-(((2R,3S)-2-(((R)-5-((benzyloxy)methyl)-2-oxooxazolidin-3-yl)methyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)amino)oxy)-2-methylpropanoate (2R,3S)-2-(((R)-5-((benzyloxy)methyl)-2-oxooxazolidin-3-yl)methyl)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonate (80 mg, 0.1 mmol) in DCM (10 mL) was added BCl3 (1 M in DCM, 0.6 mL). After stirring at rt for 15 min, the reaction mixture was quenched with EtOH and concentrated in vacuo. The crude residue was purified by reverse phase prep HPLC (XSelect CSH, 30×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 60 mL/min), affording the title compound (1.1 mg, 2%). LCMS: m/z=549.0 (M−1); 1H NMR (400 MHz, D2O): δ 6.96 (s, 1H), 5.29 (d, J=5.2 Hz, 1H), 4.48 (m, 2H), 3.73-3.35 (m, 6H), 1.36 (s, 3H), 1.35 (s, 3H).

Workup

  1. customthe reaction mixture was quenched with EtOH
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by reverse phase prep HPLC (XSelect CSH, 30×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 60 mL/min)

Sources & evidence

ORD record
ord-9296979589d04ea89d1b8cad09783686
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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