Ammonium Chloride → 439150-76-2

HRID 1958700Notes

Reaction equation

HRID 1958700 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:12](ON1C(=O)CCC1=O)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>C1COCC1.O>[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:12][OH:13])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:9])([CH3:5])([CH3:4])[CH3:6]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86641211HCID 86641211, compound

Product 1

HCID 62706972439150-76-2Yield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium borohydride (0.63 g, 16.3 mmol) was dissolved into THF (30 mL) and water (4 mL) and cooled to 0° C. (R)-4-tert-butyl 1-(2,5-dioxopyrrolidin-1-yl) 2-(tert-butoxycarbonylamino)succinate (4.6 g, 11.9 mmol) was dissolved into THF (5 mL) and added dropwise to the solution. After 1 h, saturated ammonium chloride (10 mL) was added and the mixture was extracted with ethyl acetate (4×50 mL), dried over MgSO4 and concentrated. The residue was filtered through silica gel with ethyl acetate/hexanes 1:1. The solvent was removed in vacuo to give the title compound (1.91 g, 59%) as a white foam. 1H NMR (300 MHz, DMSO-d6) δ 6.55-6.52 (m, 1H), 4.74-4.69 (m, 1H), 3.81-3.72 (m, 1H), 3.21-3.14 (m, 1H), 2.50-2.39 (m, 1H), 2.19-2.06 (m, 1H), 1.39 (s, 9H), 1.36 (s, 9H).

Workup

  1. additionadded dropwise to the solution
  2. extractionthe mixture was extracted with ethyl acetate (4×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. filtrationThe residue was filtered through silica gel with ethyl acetate/hexanes 1:1
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a3369fe66bf94b0da875dead7b2675d5
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

Loading…