Potassium Phosphate, Dibasic → Benzyl ((3S,4R)-2-oxo-4-((2-oxopyridin-1(2H)-yl)methyl)azetidin-3-yl)carbamate

HRID 708373Notes

Reaction equation

COC1C=C(OC)C=CC=1C[N:6]1[C@H:9]([CH2:10][N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[O:17])[C@H:8]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]1=[O:29].OP([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[O:29]=[C:7]1[C@@H:8]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:9]([CH2:10][N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[O:17])[NH:6]1

Participants

Conditions

Temperature: 90 °C

Procedure

Prepared in an analogous manner to example 4, step 2 using Benzyl ((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxopyridin-1(2H)-yl)methyl)azetidin-3-yl)carbamate (361 mg, 0.622 mmol), K2S2O8 (225 mg, 0.833 mmol) and K2HPO4 (135 mg, 0.773 mmol) in ACN:water (2:1, 9.9 mL) while heating for 1.5 h at 90° C. More K2S2O8 (45 mg, 0.17 mmol) and K2HPO4 (26.9 mg, 0.155 mmol) were added and heated for another 30 min, whereupon it was concentrated, redissolved in EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 0-10%) to afford the title compound (157 mg, 81%). LCMS: Rt=0.56 min, m/z=328.2 (M+1) Method 2m_acidic.

Workup

temperatureheated for another 30 min, whereupon it
concentrationwas concentrated
dissolutionredissolved in EtOAc
washwashed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 0-10%)

Sources & evidence

ORD record: ord-a6ded9f8fb2f42f2a0045da46a1d1c41
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174978B2

Reaction notes

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