Sodium Bicarbonate → Benzyl((2S,3S)-2-((R)-1,2-dihydroxyethyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamate

HRID 708321Notes

Reaction equation

HRID 708321 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[C@@H:22]1[CH2:26][O:25]C(C)(C)[O:23]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=O.[Na+]>C1COCC1.O>[OH:23][C@H:22]([C@@H:7]1[C@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9](=[O:10])[N:6]1[CH2:5][C:4]1[CH:29]=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:3]=1[O:2][CH3:1])[CH2:26][OH:25]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 13535989Benzyl((2S,3S)-1-(2,4-dimethoxybenzyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 13826541Benzyl((2S,3S)-2-((R)-1,2-dihydroxyethyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamateYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of benzyl ((2S,3S)-1-(2,4-dimethoxybenzyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-3-yl)carbamate (267 g, 0.567 mol) in THF (3 L) was added a solution of TsOH.H2O (43.6 g, 0.229 mol) in water (0.75 L). The bilayer was heated to 70° C. for 16 h then cooled to rt, neutralized to pH=7 with saturated NaHCO3 (aq) and concentrated in vacuo. The resulting mixture was filtered, washed with water and dried to afford the title compound (240 g, 98%) as a pale yellow solid. LCMS: m/z=431.1 (M+1).

Workup

  1. temperaturethen cooled to rt
  2. concentrationconcentrated in vacuo
  3. filtrationThe resulting mixture was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9ef710d9c8524e01bf04d3d9a48a6b91
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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