Hydrochloric Acid → HCID 24820744, compound

HRID 1676897Notes

Reaction equation

HRID 1676897 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Br[CH:6]([CH3:10])[C:7]([OH:9])=[O:8].C(=O)(O)[O-].[Na+].[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O.Cl>O>[C:20]([O:19][C:17]([N:4]([CH:1]1[CH2:3][CH2:2]1)[C@@H:6]([CH3:10])[C:7]([OH:9])=[O:8])=[O:16])([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 117292-Bromopropionic acidHCID 69828CyclopropylamineHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium Bicarbonate

Product 1

HCID 24820744HCID 24820744, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.5 ml (21.5 mmol, 3.85 eq) of cyclopropylamine in 1 ml of water are added 0.5 ml (5.57 mmol, 1 eq) of (+)-2-bromo-propionic acid. 2 ml of saturated sodium bicarbonate are added after 2 h, and the reaction mixture is stirred for 48 h and then concentrated. The residue is dissolved in 5 ml of 1 N sodium hydroxide and 5 ml of THF. 1.00 g (4.58 mmol, 0.82 eq) of (BOC)2O is added, and the reaction mixture is stirred for 48 h and then acidified with 1 N HCl, until the pH is acidic. The organic layer is separated, washed with 1 N HCl and brine, dried over sodium sulfate, filtered and concentrated. The residue is purified by column chromatography on silica gel (CH2Cl2/MeOH/TFA/H2O 90/10/0.5/1) to give the product.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in 5 ml of 1 N sodium hydroxide
  3. stirringthe reaction mixture is stirred for 48 h
  4. customThe organic layer is separated
  5. washwashed with 1 N HCl and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by column chromatography on silica gel (CH2Cl2/MeOH/TFA/H2O 90/10/0.5/1)
  10. customto give the product

Sources & evidence

ORD record
ord-3702836475a848899a7b45d2c03d5346
Source dataset
uspto-grants-2011_08
Patent number
US08008250B2

Reaction notes

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