Sodium Bicarbonate → 1-cyclopentyl N-{3-[(methylamino)methyl]benzyl}-L-leucinate

HRID 632576

Reaction equation

HRID 632576 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:22]1([O:27][C:28](=[O:35])[C@H:29]([CH2:31][CH:32]([CH3:34])[CH3:33])[NH2:30])[CH2:26][CH2:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[CH3:51][NH2:52].C(=O)([O-])O.[Na+]>ClC(Cl)C.CO.C(OCC)(=O)C>[CH3:51][NH:52][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:30][C@H:29]([C:28]([O:27][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:35])[CH2:31][CH:32]([CH3:33])[CH3:34]

Participants

9

Reactant 5

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 71278253-(Bromomethyl)benzaldehydeHCID 86633653L-leucine cyclopentyl ester tosylate

Product 1

HCID 866864261-cyclopentyl N-{3-[(methylamino)methyl]benzyl}-L-leucinateYield 15.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(bromomethyl)-benzaldehyde (0.513 g, 2.57 mmol) in dichloroethane (10 mL) was added L-leucine cyclopentyl ester tosylate (1.29 g, 3.46 mmol) and sodium triacetoxyborohydride (1.37 g, 6.46 mmol). The mixture was stirred for 30 minutes at room temperature then poured into ethyl acetate (200 mL). The organic extracts were washed with saturated ammonium chloride (2 times 50 mL) and water (50 mL). The organic extracts were then dried (MgSO4) and concentrated. The residue was dissolved in ethanol (30 mL) and methylamine hydrochloride (4.17 g, 61.7 mmol) was added followed by sodium hydrogen carbonate (4.32 g, 51 mmol). The mixture was stirred at room temperature for 18 hours then concentrated under vacuum, loaded directly onto a silica gel column and eluted with 95:5 dichloromethane:methanol to yield the desired product (0.130 g, 15% yield). LC/MS: m/z 333.25 [M+H]+

Workup

  1. washThe organic extracts were washed with saturated ammonium chloride (2 times 50 mL) and water (50 mL)
  2. dry with materialThe organic extracts were then dried (MgSO4)
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethanol (30 mL)
  5. stirringThe mixture was stirred at room temperature for 18 hours
  6. concentrationthen concentrated under vacuum
  7. washeluted with 95:5 dichloromethane

Sources & evidence

ORD record
ord-91e262448bd24c2a981e1bc01796de64
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Linked notes

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