Triphenylphosphine → HCID 71290288, compound

HRID 536520Notes

Reaction equation

HRID 536520 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[N:12]=[C:13]([OH:23])[C:14]3[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:15]=3[N:16]=1)[N:6]=[C:5]2[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31].[F:32][C:33]([F:38])([F:37])[CH2:34][CH2:35]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[N:12]=[C:13]([O:23][CH2:35][CH2:34][C:33]([F:38])([F:37])[F:32])[C:14]3[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:15]=3[N:16]=1)[N:6]=[C:5]2[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 1375123,3,3-Trifluoro-1-propanol2×HCID 178429273HCID 178429273, compound

Product 1

HCID 71290288HCID 71290288, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 80 mg (0.19 mmol) of the compound from example 31 was largely dissolved in 2 ml THF, 32.5 mg (0.29 mmol) of 3,3,3-trifluoropropan-1-ol, 75 mg (0.29 mmol) of triphenyl phosphine and 56 μl (0.29 mmol) of diisopropyl azodicarboxylate were added and it was stirred for 3 d at RT. A further 11 mg (0.01 mmol) of 3,3,3-trifluoropropan-1-ol, 25 mg (0.01 mmol) of triphenyl phosphine and 19 μl (0.01 mmol) of diisopropyl azodicarboxylate were added and it was stirred for 1 d at RT. The reaction mixture was concentrated by evaporation and the residue was purified by preparative HPLC (Reprosil C18, gradient of acetonitrile/0.01% aq. formic acid). Yield: 48 mg (49% of theor.)

Workup

  1. stirringit was stirred for 1 d at RT
  2. concentrationThe reaction mixture was concentrated by evaporation
  3. customthe residue was purified by preparative HPLC (Reprosil C18, gradient of acetonitrile/0.01% aq. formic acid)

Sources & evidence

ORD record
ord-0be01bc5078e4583a9d66b6fdb144cba
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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