Sodium Carbonate → (2R)-2-({Formyl[(phenylmethyl)oxy]amino}methyl)hexanoic acid

HRID 1396863Notes

Reaction equation

HRID 1396863 reaction equation
N1([CH:10]=[O:11])C2C=CC=CC=2N=N1.[C:12]1([CH2:18][O:19][NH:20][CH2:21][C@@H:22]([CH2:26][CH2:27][CH2:28][CH3:29])[C:23]([OH:25])=[O:24])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>C1COCC1.O>[CH:10]([N:20]([CH2:21][C@@H:22]([CH2:26][CH2:27][CH2:28][CH3:29])[C:23]([OH:25])=[O:24])[O:19][CH2:18][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:11]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 11694494(2R)-2-({[(Phenylmethyl)oxy]amino}methyl)hexanoic acid

Product 1

HCID 11185069(2R)-2-({Formyl[(phenylmethyl)oxy]amino}methyl)hexanoic acidYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1H-1,2,3-benzotriazole-1-carbaldehyde (26 g, 0.18 mol) in THF (200 ml) at 0° C. was added dropwise a solution of (2R)-2-({[(phenylmethyl)oxy]amino}methyl)hexanoic acid (8) (40 g, 0.16 mol) in THF (200 mL). The reaction mixture was warmed up to rt and stirred overnight. LC/MS indicated completion of the reaction. To the reaction mixture at 0° C. was added water (400 mL), Na2CO3 (36 g), and Boc2O (43.6 g, 0.36 mol). The mixture was stirred for 3 h. THF was removed under vacuum. The aqueous mixture was washed with ether and then acidified to pH ˜2.0 with acetic acid, and extracted with ethyl acetate. The extracts were dried and concentrated to provide the title compound (36.8 g, 80%). LCMS: (M+H)+: 280.2.

Workup

  1. customcompletion of the reaction
  2. stirringThe mixture was stirred for 3 h
  3. customTHF was removed under vacuum
  4. washThe aqueous mixture was washed with ether
  5. extractionextracted with ethyl acetate
  6. customThe extracts were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ce809a6a3427457a96ebb690d2c84eb9
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

Loading…