Water → HCID 86613676, compound

HRID 273471Notes

Reaction equation

HRID 273471 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:11]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][N:13]=2)[C@@H:10]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[C:9]1=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:31][C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+].O>C(OC(C)C)(C)C>[C:1]([O:5][C:6]([NH:8][C@@H:11]([C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][N:13]=1)[C@@H:10]([O:19][Si:20]([CH:24]([CH3:25])[CH3:26])([CH:21]([CH3:22])[CH3:23])[CH:27]([CH3:29])[CH3:28])[C:9](=[O:30])[S:38][C:35]1[CH:36]=[CH:37][C:32]([Br:31])=[CH:33][CH:34]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 12098273HCID 12098273, compound3×

Product 1

HCID 86613676HCID 86613676, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent2×

Procedure

A concentrated residue (70.9 mmol) of (3R,4S)-1-(tert-butoxycarbonyl)-4-(3-fluoro-2-pyridyl)-3-triisopropylsilyloxy-2-azetidinone (compound 20) was dissolved in diisopropyl ether (240 mL), and 4-bromothiophenol (15.5 g, 82.0 mmol) and potassium carbonate (3 g) were added thereto, and stirred at room temperature for 25 minutes. The disappearance of (3R,4S)-1-(tert-butoxycarbonyl)-4-(3-fluoro-2-pyridyl)-3-triisopropylsilyloxy-2-azetidinone was confirmed, and then water (200 mL) and diisopropyl ether (120 mL) were added thereto and subjected to liquid-liquid separation. The organic layer was separated, washed with water (150 mL) and then with saturated saline water (150 mL), dried over magnesium sulfate, and concentrated under reduced pressure to obtain a residue of S-(4-bromophenyl) (2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluoro-2-pyridinyl)-2-[(triisopropylsilyl)oxy]propanethioate (compound 14) (45.3 g).

Workup

  1. customsubjected to liquid-liquid separation
  2. customThe organic layer was separated
  3. washwashed with water (150 mL)
  4. dry with materialwith saturated saline water (150 mL), dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46a5af0bbf044b02bdf0d1f6e572392a
Source dataset
uspto-grants-2008_11
Patent number
US07456302B2

Reaction notes

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