Hydrochloric Acid → HCID 58313086, compound

HRID 454431Notes

Reaction equation

HRID 454431 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:4][C@@H:3]([C:11]([O:13]CC)=[O:12])[N:2]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].O.[OH-].[Li+].Cl>C1COCC1.O.CO>[C:20]1([CH2:19][O:18][C:16]([N:2]2[C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]3([CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)[CH2:1]2)=[O:17])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58313162HCID 58313162, compound

Product 1

HCID 58313086HCID 58313086, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 3-ethyl 2-(phenylmethyl) (3S)-8-oxa-2-azaspiro[4.5]decane-2,3-dicarboxylate (120) (300 mg, 0.86 mmol) in THF/water/methanol (3 mL/1.5 mL/1.5 mL) was added lithium hydroxide monohydrate (72 mg, 1.7 mmol) and the reaction stirred at room temperature for 30 min. The reaction was treated with 1N HCl (2 mL) and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the organic layer dried over MgSO4 and concentrated in vacuo to afford the title compound in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.54-12.93 (m, 1H) 7.21-7.47 (m, 5H) 4.90-5.20 (m, 2H) 4.11-4.41 (m, 1H) 3.44-3.70 (m, 5H) 3.24 (dd, J=15.0, 11.7 Hz, 1H) 2.32 (td, J=13.6, 8.5 Hz, 1H) 1.73 (ddd, J=16.8, 12.9, 7.2 Hz, 1H) 1.38-1.64 (m, 4H). LC-MS ESI (M−H)−=318.19.

Workup

  1. custompartitioned between EtOAc and water
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe organic layer dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b38e959a78e7451fbc9db19023cf4e7c
Source dataset
uspto-grants-2013_07
Patent number
US08492554B2

Reaction notes

Loading…