Sodium Hydroxide → HCID 67480625, compound

HRID 2274306Notes

Reaction equation

HRID 2274306 reaction equation
[CH2:1]([O:8][CH:9]1[CH:14]2[NH:15]C(=O)[O:17][CH:13]2[CH2:12][CH:11]([CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH2:15][CH:14]1[CH:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:11]([CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH:13]1[OH:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67480431HCID 67480431, compound

Product 1

HCID 67480625HCID 67480625, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of rac-(3 aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-hexahydrobenzo[d]oxazol-2(3H)-one (280 mg, 0.592 mmol) in ethanol (2 mL) was added 2 N NaOH (10 mL). The mixture was heated at reflux for 16 h. After cooling to room temperature, the mixture was extracted with DCM (3×15 mL). The combined extracts were washed with brine and dried over Na2SO4. Solvents were evaporated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with 5% MeOH in DCM and 94:4:2 DCM-MeOH—NH4OH (28% aqueous) to give rac-(1R,2R,3S,4S,5S)-2-amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol (Intermediate Example 2) (227 mg, 86%) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.37-7.25 (m, 15H), 5.01 (d, J=11.5 Hz, 1H), 4.84 (d, J=10.9 Hz, 1H), 4.63 (d, J=11.5 Hz, 1H), 4.60 (d, J=10.9 Hz, 1H), 4.47 (s, 2H), 3.86 (q, J=2.8 Hz, 1H), 3.79 (dd, J=9.0, 4.2 Hz, 1H), 3.58-3.53 (m, 2H), 3.44 (dd, J=9.0, 2.5 Hz, 1H), 2.85 (d, J=6.7 Hz, 1H), 2.27-2.15 (m, 1H), 1.94 (dt, J=14.5, 3.5 Hz, 1H), 1.67 (ddd, J=14.8, 12.6 Hz, 2.4, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionthe mixture was extracted with DCM (3×15 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customSolvents were evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. washeluted with 5% MeOH in DCM and 94:4:2 DCM-MeOH—NH4OH (28% aqueous)

Sources & evidence

ORD record
ord-1382b78bf98d497d9bc92502380d29de
Source dataset
uspto-grants-2015_09
Patent number
US09126957B2

Reaction notes

Loading…