Sodium Bicarbonate → (R)-benzyl 1-(4-chlorobutanamido)-3-hydroxypropan-2-ylcarbamate

HRID 451819Notes

Reaction equation

HRID 451819 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:17][NH:18][C:19](=[O:24])[CH2:20][CH2:21][CH2:22][Cl:23])[C:13](OC)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[Cl:23][CH2:22][CH2:21][CH2:20][C:19]([NH:18][CH2:17][C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][OH:14])=[O:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 59201592HCID 59201592, compound

Product 1

HCID 86639450(R)-benzyl 1-(4-chlorobutanamido)-3-hydroxypropan-2-ylcarbamateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-methyl 2-(benzyloxycarbonylamino)-3-(4-chlorobutanamido)propanoate (5.0 g, 14 mmol) in 100 mL of anhydrous MeOH was added NaBH4 (12.9 g, 0.33 mol) and the mixture was stirred at it overnight. The pH of the reaction mixture was adjusted to 8-9 using NaHCO3, the mixture was evaporated to near dryness, followed by extraction with EtOAc. The organic layer was washed with water, dried over Na2SO4, filtered and concentrated to give (R)-benzyl 1-(4-chlorobutanamido)-3-hydroxypropan-2-ylcarbamate (3.9 g, yield 85%) that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 7.37-7.30 (m, 5H) 5.13 (d, 2H), 3.77 (m, 1H), 3.57 (m, 4H), 2.32 (t, 2H), 2.08 (t, 2H).

Workup

  1. customthe mixture was evaporated
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ad12cc33fd41444ba8d4e1d5cdcbac6b
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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