Water → HCID 86677883, compound

HRID 1499961Notes

Reaction equation

HRID 1499961 reaction equation
[N:1]([CH:4]([C:14]1[C:15]([O:25][CH2:26][CH3:27])=[C:16]([C:22](=[O:24])[CH3:23])[CH:17]=[C:18]([Cl:21])[C:19]=1[F:20])[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.[Cl-].[Na+].O>[NH2:1][CH:4]([C:14]1[C:15]([O:25][CH2:26][CH3:27])=[C:16]([C:22](=[O:24])[CH3:23])[CH:17]=[C:18]([Cl:21])[C:19]=1[F:20])[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86677882HCID 86677882, compound

Product 1

HCID 86677883HCID 86677883, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

1-[3-(1-Azido-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-5-chloro-2-ethoxy-4-fluorophenyl]ethanone (750 mg, 1.8 mmol) (from Step 5) was stirred in tetrahydrofuran (10 mL) with water (0.33 mL) and triphenylphosphine was added. The mixture was heated to 60° C. for 2 hours and cooled to rt. Brine was added and the mixture was extracted with ethyl acetate. The extracts were dried over sodium sulfate, filtered and evaporated to give the desired compound 700 mg, 100%. LCMS calculated for C18H30ClFNO3Si (M+H)+: m/z=390.2; found: 390.2.

Workup

  1. additionwas added
  2. temperaturecooled to rt
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7b21bfd4b626467bac8044993d325c3b
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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