Triphenylphosphine → (R)-methyl 3-(4-(trifluoromethyl)phenoxy)-2-(tritylamino)propanoate

HRID 1425925Notes

Reaction equation

HRID 1425925 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[F:32][C:33]([F:42])([F:41])[C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1.O[CH2:44][C@@H:45]([NH:50][C:51]([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]([O:48][CH3:49])=[O:47]>C1COCC1>[F:32][C:33]([F:41])([F:42])[C:34]1[CH:35]=[CH:36][C:37]([O:40][CH2:44][C@@H:45]([NH:50][C:51]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:46]([O:48][CH3:49])=[O:47])=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 5462977Diethyl azodicarboxylateHCID 7438296Methyl trityl-D-serinate

Product 1

HCID 68281332(R)-methyl 3-(4-(trifluoromethyl)phenoxy)-2-(tritylamino)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenylphosphine (3 eq) in dry THF under Argon was added diethylazodicarboxylate (3 eq) dropwise. The reaction mixture was stirred at room temperature for 15 minutes before adding a solution of 4-(trifluoromethyl)phenol (3 eq in dry THF) dropwise. The reaction mixture was stirred at room temperature for 1 hour before adding (R)-methyl 3-hydroxy-2-(tritylamino)propanoate (LXXXIX) in dry THF in one portion. The reaction mixture was stirred at room temperature ovenight. The mixture was concentrated to dryness, treated with hexane and filtered. The residue was concentrated to dryness and purified by silica flash chromatography (EtOAc/hexane=1:5). Pure (R)-methyl 3-(4-(trifluoromethyl)phenoxy)-2-(tritylamino)propanoate (XC) was obtained as an off-white solid (50% yield).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. stirringThe reaction mixture was stirred at room temperature ovenight
  3. concentrationThe mixture was concentrated to dryness
  4. additiontreated with hexane
  5. filtrationfiltered
  6. concentrationThe residue was concentrated to dryness
  7. custompurified by silica flash chromatography (EtOAc/hexane=1:5)

Sources & evidence

ORD record
ord-ff12b31fb3c54007a20247ca4a0a8295
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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