tert-butyl N-(2-oxoethyl)carbamate → HCID 118379312, compound

HRID 708443Notes

Reaction equation

HRID 708443 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][C@@H:6]1[C@H:9]([NH:10][C:11](=[O:38])/[C:12](=[N:26]\[O:27][C:28]([CH3:37])([CH3:36])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])/[C:13]2[N:14]=[C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[S:16][CH:17]=2)[C:8](=[O:39])[NH:7]1.[C:40]([O:44][C:45](=[O:50])[NH:46][CH2:47][CH:48]=O)([CH3:43])([CH3:42])[CH3:41].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:22]([O:21][C:19]([NH:18][C:15]1[S:16][CH:17]=[C:13](/[C:12](=[N:26]/[O:27][C:28]([CH3:37])([CH3:36])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])/[C:11]([NH:10][C@@H:9]2[C:8](=[O:39])[NH:7][C@@H:6]2[CH2:5][NH:4][CH2:3][CH2:2][NH:1][CH2:48][CH2:47][NH:46][C:45](=[O:50])[O:44][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[N:14]=1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 118380329HCID 118380329, compound

Product 1

HCID 118379312HCID 118379312, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of tert-butyl 2-(((Z)-(2-(((2R,3S)-2-(((2-aminoethyl)amino)methyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)amino)oxy)-2-methylpropanoate (100 mg, 0.176 mmol) in DCE (1.8 mL) was added tert-butyl(2-oxoethyl)carbamate (27.9 mg, 0.176 mmol). After stirring for 2 h, sodium triacetoxyborohydride (112 mg, 0.527 mmol) was added. After 12 h, the reaction mixture was quenched with saturated NaHCO3 (aq) and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. It was used as crude in step 2.

Workup

  1. waitAfter 12 h
  2. customthe reaction mixture was quenched with saturated NaHCO3 (aq)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdc455a0053b448691d02e8f35be65eb
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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