Water → HCID 66749849, compound

HRID 1893658Notes

Reaction equation

HRID 1893658 reaction equation
[NH2:1][CH:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].O.[O:11]1[CH2:15][CH2:14][CH:13]([O:16][C:17](=O)[O:18]C2C=CC([N+]([O-])=O)=CC=2)[CH2:12]1.CCN(C(C)C)C(C)C>CC#N.CO>[CH3:7][C:6]([CH3:9])([CH3:8])[CH:2]([NH:1][C:17]([O:16][CH:13]1[CH2:14][CH2:15][O:11][CH2:12]1)=[O:18])[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 3061312-Amino-3,3-dimethylbutanoic acidHCID 15343685HCID 15343685, compound

Product 1

HCID 66749849HCID 66749849, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

2-Amino-3,3-dimethyl-butyric acid (551 mg, 4.2 mmol) was dissolved in CH3CN (15 mL), H2O (3 mL) and MeOH (3 mL). Carbonic acid 4-nitro-phenyl ester tetrahydro-furan-3-yl ester (1.6 g, 6.3 mmol) and DIEA (1.46 mL, 8.4 mmol) were added. This reaction mixture was allowed to stir at room temperature for 16 h. After concentrated, diluted with EtOAc, washed with brine and H2O, dried over Na2SO4, the crude product was purified on silica (12 g, 25-75% EtOAc/hexanes) to give intermediate 3,3-dimethyl-2-(tetrahydro-furan-3-yloxycarbonylamino)-butyric acid as a white solid (670 mg, 65%).

Workup

  1. concentrationAfter concentrated
  2. additiondiluted with EtOAc
  3. washwashed with brine and H2O
  4. dry with materialdried over Na2SO4
  5. customthe crude product was purified on silica (12 g, 25-75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d7579fbc2d31484799ddf52ffd4fcc1f
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

Loading…