Sodium borohydride → HCID 118379551, compound

HRID 708461Notes

Reaction equation

HRID 708461 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:15](=[O:16])[NH:14][C@@H:13]1[CH2:17][N:18]1[C:22](=[O:23])[CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:19]1=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:15](=[O:16])[NH:14][C@@H:13]1[CH2:17][N:18]1[CH:22]([OH:23])[CH2:21][N:20]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C:19]1=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118379844HCID 118379844, compound

Product 1

HCID 118379551HCID 118379551, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 3-(((2R,3S)-3-(((benzyloxy)carbonyl)amino)-4-oxoazetidin-2-yl)methyl)-2,4-dioxoimidazolidine-1-carboxylate (170 mg, 0.390 mmol) in EtOH (10 mL) at 0° C. was added sodium borohydride (30 mg, 0.78 mmol). After 3 h at 0° C., the mixture was quenched with saturated NH4Cl (aq) and partially concentrated in vacuo. The bilayer was extracted with DCM and the organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting residue was used as such in step 5. LCMS: m/z=457.1 (M+Na).

Workup

  1. customthe mixture was quenched with saturated NH4Cl (aq)
  2. concentrationpartially concentrated in vacuo
  3. extractionThe bilayer was extracted with DCM
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2854aa94bb9f4354823255bd0b09749d
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

Loading…