Nitrogen → HCID 86698884, compound

HRID 527240Notes

Reaction equation

HRID 527240 reaction equation
N#N.[Si:3]([O:10][CH2:11][C:12]1[O:13][CH:14]=[C:15]([C:17]2([OH:20])[CH2:19][CH2:18]2)[N:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[C:21](Cl)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>N1C=CC=CC=1.CC(=O)OCC>[C:21]([O:20][C:17]1([C:15]2[N:16]=[C:12]([CH2:11][O:10][Si:3]([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4])[O:13][CH:14]=2)[CH2:18][CH2:19]1)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 86698881HCID 86698881, compound

Product 1

HCID 86698884HCID 86698884, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(2-(((tert-butyldimethylsilyl)oxy)methyl)oxazol-4-yl)cyclopropanol (509 mg, 1.89 mmol) in pyridine (2.0 mL) was treated with pivaloyl chloride (0.28 mL, 2.27 mmol) and the reaction mixture was stirred at rt overnight. Sat. aq. NH4Cl (10 mL) was added followed by EA (10 mL). The org. layer was washed with a CuSO4 sol. (2×15 mL) followed by brine (10 mL). The layers were separated and the org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (9:1 hept-EA) gave the title compound as a colorless oil: TLC: rf (9:1 hept-EA)=0.35. LC-MS-conditions 06: tR=1.19 min, [M+H]+=354.18.

Workup

  1. washlayer was washed with a CuSO4 sol. (2×15 mL)
  2. customThe layers were separated
  3. dry with materiallayer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (9:1 hept-EA)

Sources & evidence

ORD record
ord-22cc4da0590b4edd8a43c12d2af70a20
Source dataset
uspto-grants-2016_05
Patent number
US09346793B2

Reaction notes

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