Ethyl Acetate → HCID 68284162, compound

HRID 1527422Notes

Reaction equation

HRID 1527422 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][C@@:10]2([CH2:12][OH:13])[C@H:8]([CH2:9]2)[N:7]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:5])C.[OH-].[Na+].OS([O-])(=O)=O.[K+].CCOC(C)=O>C1COCC1.O>[C:17]([O:16][C:14]([N:7]1[C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][C@@:10]2([CH2:12][OH:13])[C@@H:8]1[CH2:9]2)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 68283566HCID 68283566, compound

Product 1

HCID 68284162HCID 68284162, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a diastereoisomeric mixture of (1R,3S,5S) and (1S,3S,5R)-5-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (ratio 4:6, 100 mg, 0.31 mmol) in THF (1.5 mL) and H2O (0.15 mL) at 0° C. was added NaOH (1 M in water, 0.63 mL, 0.63 mmol). The solution was stirred 1 h at RT and poured into 10% KHSO4 (until pH 1), EtOAc was added and the layers were separated (×3). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude residue was used without further purification in the next step. MS (HPLC/MS): 256.2 [M−H]−, 258.3 [M+H]+, 280.3 [M+Na]+, 200.2 [MH−tBu]+, 515.54 [2M+H]+, 537.4 [2M+Na]+; tR (HPLC conditions f): 1.28 min.

Workup

  1. additionwas added
  2. customthe layers were separated (×3)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was used without further purification in the next step
  7. custom1.28 min.

Sources & evidence

ORD record
ord-9fa986c0421446238825bc2a9e81f359
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…