Trifluoroacetic acid → HCID 57989074, compound

HRID 470960Notes

Reaction equation

HRID 470960 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH2:9][CH2:10][C:11]1[CH:38]=[CH:37][C:14]([O:15][CH2:16][CH2:17][NH+:18]2[CH2:36][CH2:35][C:21]3([O:26][CH2:25][CH2:24][N:23]([C:27]([C:29]4[N:30]=[C:31]([CH3:34])[S:32][CH:33]=4)=[O:28])[CH2:22]3)[CH2:20][CH2:19]2)=[CH:13][CH:12]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCOCC>[CH3:34][C:31]1[S:32][CH:33]=[C:29]([C:27]([N:23]2[CH2:22][C:21]3([CH2:35][CH2:36][N:18]([CH2:17][CH2:16][O:15][C:14]4[CH:37]=[CH:38][C:11]([CH2:10][CH:9]=[O:8])=[CH:12][CH:13]=4)[CH2:19][CH2:20]3)[O:26][CH2:25][CH2:24]2)=[O:28])[N:30]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86636749HCID 86636749, compound

Product 1

HCID 57989074HCID 57989074, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.04 mL) was added to a solution of 9-(2-(4-(2-hydroxyethyl)phenoxy)ethyl)-4-(2-methylthiazole-4-carbonyl)-1-oxa-4-aza-9-azoniaspiro[5.5]undecane (example 3, step c) (0.22 g) in DCM (3 mL) and the resulting mixture was stirred for 5 min. Dess-Martin periodinane (0.31 g) was then added and the resulting mixture stirred for 5 min. A mixture of saturated sodium thiosulphate solution (0.5 mL), sodium bicarbonate solution (0.5 mL) and ether (5 mL) was then added and the resulting mixture stirred for 5 min. The organic layer was separated and washed with sodium bicarbonate solution (1 mL) and water (1 mL), then dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a clear oil which was used immediately. Yield 0.19 g.

Workup

  1. stirringthe resulting mixture stirred for 5 min
  2. additionwas then added
  3. stirringthe resulting mixture stirred for 5 min
  4. customThe organic layer was separated
  5. washwashed with sodium bicarbonate solution (1 mL) and water (1 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-87dea1c799524f9a9ca64a070ddc1d0a
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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