Potassium Phosphate, Dibasic → HCID 118379379, compound

HRID 708535Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:22]=[N:21][N:20]([CH2:23][C@@H:24]3[C@H:27]([NH:28][C:29]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])[C:26](=[O:39])[N:25]3CC3C=CC(OC)=CC=3OC)[N:19]=2)=[O:15])[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].OP([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:11][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:22]=[N:21][N:20]([CH2:23][C@@H:24]3[C@H:27]([NH:28][C:29]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:30])[C:26](=[O:39])[NH:25]3)[N:19]=2)=[O:15])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

Prepared in an anologous manner as example 4, step 2 using (2-(((2R,3S)-3-(((benzyloxy)carbonyl)amino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-2-yl)methyl)-2H-1,2,3-triazol-4-yl)methyl 3-(((tert-butoxycarbonyl)amino)methyl)azetidine-1-carboxylate (410 mg, 0.591 mmol), K2S2O8 (272 mg, 1.01 mmol) and K2HPO4 (165 mg, 0.946 mmol) in ACN:water (2:1, 7.2 mL) while heating for 5 h at 90° C. The crude residue was purified via silica gel chromatography (EtOAc-Heptane, 30-90%), affording the title compound (80 mg, 25%) as a solid. LCMS: Rt=0.78 min, m/z=544.2 (M+1) Method 2m_acidic.

Workup

customThe crude residue was purified via silica gel chromatography (EtOAc-Heptane, 30-90%)

Sources & evidence

ORD record: ord-2a37a1289fc14903b991b63c8ebf7fc1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174978B2

Reaction notes

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