Sodium Bicarbonate → HCID 67288485, compound

HRID 403284Notes

Reaction equation

HRID 403284 reaction equation
[CH3:1][NH:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[CH2:4]1.[C:16]([N:23]1[CH2:26][CH2:25][C:24]1=O)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(O)(=O)C>[C:19]([O:18][C:16]([N:23]1[CH2:26][CH:25]([N:2]([C@H:3]2[CH2:7][CH2:6][N:5]([C:8](=[O:9])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:4]2)[CH3:1])[CH2:24]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23179885tert-Butyl 2-oxoazetidine-1-carboxylateHCID 67289029HCID 67289029, compound

Product 1

HCID 67288485HCID 67288485, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

To a solution of compound 4d (TFA salt, 124 mg, 0.39 mmol) and compound 1e (94 mg, 0.55 mmol) in 1,2-DCE (2 mL) was added acetic acid (0.1 mL). To this mixture was added Na(OAc)3BH (132 mg, 0.624 mmol). The reaction was stirred at room temperature for 4 h. To the reaction mixture was added aq. NaHCO3, and the resultant mixture was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated. Purification by flash column chromatography (silica gel, 5% MeOH/EtOAc+0.5% TEA) gave compound 4e (0.11 g). MS m/z (M+H+) 360.5.

Workup

  1. extractionthe resultant mixture was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (silica gel, 5% MeOH/EtOAc+0.5% TEA)

Sources & evidence

ORD record
ord-9c5af66258544ff583ec2231abf287fb
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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