Water → HCID 86672462, compound

HRID 72878Notes

Reaction equation

HRID 72878 reaction equation
[F:1][CH:2]([F:30])[CH2:3][N:4]1[CH2:9][C:8]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[O:7][CH:6]([C:22](=[O:29])[NH:23][CH2:24][CH:25]([OH:28])CO)[CH2:5]1.O>C1COCC1>[F:30][CH:2]([F:1])[CH2:3][N:4]1[CH2:9][C:8]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[O:7][CH:6]([C:22](=[O:29])[NH:23][CH2:24][CH:25]=[O:28])[CH2:5]1

Participants

4

Reactant 2

HCID 962WaterHCID 86672463HCID 86672463, compound

Product 1

HCID 86672462HCID 86672462, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 4-(2,2-difluoroethyl)-2-((2,3-dihydroxypropyl)carbamoyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (422 mg, 0.96 mmol) in THF (10 mL) was added NaIO4 (522 mg, 2.44 mmol) followed by H2O (4 mL) the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered and partitioned between sat. aq. sodium bicarbonate/ethyl acetate. The aqueous layer was extracted further with ethyl acetate (3×50 mL). The organics were combined, washed with sat. aq. sodium bicarbonate (50 mL), dried over MgSO4, and concentrated in vacuo to yield tert-butyl 4-(2,2-difluoroethyl)-2-((2-oxoethyl)carbamoyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (377 mg, 96%) as a white solid, which was taken onto the next step without purification. ESI-MS m/z calc. 405.2. Found 406.5 (M+1)+; Retention time: 1.32 minutes (3 min run)

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompartitioned between sat. aq. sodium bicarbonate/ethyl acetate
  3. extractionThe aqueous layer was extracted further with ethyl acetate (3×50 mL)
  4. washwashed with sat. aq. sodium bicarbonate (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd0a84a502724bf0a073fa5c87104b58
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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