Hydrochloric Acid → HCID 58313066, compound

HRID 709363Notes

Reaction equation

HRID 709363 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:22]([CH3:24])[CH3:23])[C:7]([N:9]1[C@H:17]([C:18]([O:20]C)=[O:19])[CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10]1)=[O:8])=[O:4].C(O)(C)(C)C.[Li+].[OH-].Cl>CCOC(C)=O>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:22]([CH3:24])[CH3:23])[C:7]([N:9]1[C@H:17]([C:18]([OH:20])=[O:19])[CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10]1)=[O:8])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6386tert-ButanolHCID 58313131HCID 58313131, compound

Product 1

HCID 58313066HCID 58313066, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 10 mL round-bottomed flask, (S)-methyl 7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxylate (150 mg, 436 μmol) was combined with tert-butanol (250 μl) to give a colorless solution. LiOH (1M, 871 μl, Eq: 2) was added and stirred at room temperature for 2 hr. It was acidified with 1N HCl to pH 3 and diluted with 100 ml of EtOAc. It was washed with brine (5 ml), dried with MgSO4, filtered and concentrated in vacuo to afford (S)-7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxylic acid as a white solid which was used for the next reaction without further purification. (75 mg, 52.1%).

Workup

  1. customto give a colorless solution
  2. washIt was washed with brine (5 ml)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9485a99db93149a9b4a20cbdd066828a
Source dataset
uspto-grants-2015_11
Patent number
US09180193B2

Reaction notes

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