HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → 1-Phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-hydroxy-4-aza-octane

HRID 232174
Notes
Print preview

Reaction equation

HRID 232174 reaction equation
[C:1]1(=[O:39])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:10][C:11]([F:23])([F:22])[CH2:12][CH2:13][O:14]CC2C=CC=CC=2)[C:4](=[O:34])[C:3]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:2]12.C[Si](I)(C)C.C(N(CC)CC)C.Cl>ClCCl.CO>[C:4]1(=[O:34])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)(=[O:25])=[O:26])[CH2:10][C:11]([F:23])([F:22])[CH2:12][CH2:13][OH:14])[C:1](=[O:39])[C:2]2=[CH:38][CH:37]=[CH:36][CH:35]=[C:3]12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 85247Trimethylsilyl iodideHCID 198607071-Phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-benzyloxy-4-aza-octane

Product 1

HCID 198606861-Phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-hydroxy-4-aza-octane

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
2×
HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-benzyloxy-4-aza-octane (9.5 g, 17.1 mM) and trimethylsilyl iodide (2.7 mL, 10% excess) in dry dichloromethane is stirred overnight at room temperature under nitrogen. Triethylamine (3 g) is added, and stirring is continued for 1 hour at room temperature. Following the addition of more dichloromethane, the reaction mixture is washed with 1N HCl (twice), aqueous NaHSO3 (twice), brine (twice), and dried (Na2SO4). The solvents are removed by evaporation to yield an oil. This oil is dissolved in methanol and 1 mL of a 9N solution of HCl in methanol is added. The mixture is evaporated and stripped twice with CCl4 to provide an oil, which upon scratching with ether/petroleum ether yields 1-phthalimido-4-p-toluenesulfonyl-6,6-difluoro-8-hydroxy-4-aza-octane as slightly violet crystals: 6.8 g (85%).

Workup

  1. washthe reaction mixture is washed with 1N HCl (twice), aqueous NaHSO3 (twice), brine (twice), and
  2. dry with materialdried (Na2SO4)
  3. customThe solvents are removed by evaporation
  4. customto yield an oil
  5. customThe mixture is evaporated
  6. customto provide an oil, which

Sources & evidence

ORD record
ord-63b58cfa5b874ce582f39f79f80b2c42
Source dataset
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04851448

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes