Lithium Hydroxide → HCID 58313160, compound

HRID 709367Notes

Reaction equation

HRID 709367 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:24]([CH3:26])[CH3:25])[C:7]([N:9]1[C@H:13]([C:14]([O:16]CC)=[O:15])[CH2:12][C:11]2([CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH2:10]1)=[O:8])=[O:4].C1COCC1.[Li+].[OH-]>C(O)(C)(C)C>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:24]([CH3:26])[CH3:25])[C:7]([N:9]1[CH:13]([C:14]([OH:16])=[O:15])[CH2:12][C:11]2([CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[CH2:10]1)=[O:8])=[O:4]

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 8028TetrahydrofuranHCID 86670839HCID 86670839, compound

Product 1

HCID 58313160HCID 58313160, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In a 10 mL round-bottomed flask, (S)-ethyl 2-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-8-oxa-2-azaspiro[4.5]decane-3-carboxylate (300 mg, 810 μmol) was combined with THF 6(ml) and tert-butanol (1 ml) to give a colorless solution. LiOH (1.0M, 1.62 ml, 1.62 mmol, Eq: 2) was added and stirred at room temperature for 2 hr. Then more LiOH (1.0M, 1 ml, 1 mmol) was added and stirred for an another 2 hr. THF was removed and the aqueous was acidified with 1N HCl to pH=3 and diluted with EtOAc (100 ml). It was washed with brine (10 ml), dried with MgSO4, filtered and concentrated to afford 2-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-8-oxa-2-azaspiro[4.5]decane-3-carboxylic acid as a white solid (270 mg, 97.4%). ESI-LRMS m/e calcd for C16H26N2O6 [M+] 342. found 341 [M+H+].

Workup

  1. customto give a colorless solution
  2. stirringstirred for an another 2 hr
  3. customTHF was removed
  4. additiondiluted with EtOAc (100 ml)
  5. washIt was washed with brine (10 ml)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2bcd98796a5e4a08a37aed8e4a954518
Source dataset
uspto-grants-2015_11
Patent number
US09180193B2

Reaction notes

Loading…