Triphenylphosphine → {[2-(3-Benzyloxy-5-fluoro-phenyl)-1-oxiranyl-ethylcarbamoyl]-methyl}-carbamic acid benzyl ester

HRID 2117288Notes

Reaction equation

HRID 2117288 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH2:34]([O:41][C:42](=[O:69])[NH:43][CH2:44][C:45](=[O:68])[NH:46][CH:47]([CH2:52][C:53]1[CH:58]=[C:57]([F:59])[CH:56]=[C:55]([O:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[CH:54]=1)[CH:48]([OH:51])[CH2:49]O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[O-][Mn](=O)(=O)=O.[K+]>C(Cl)(Cl)Cl>[CH2:34]([O:41][C:42](=[O:69])[NH:43][CH2:44][C:45](=[O:68])[NH:46][CH:47]([CH:48]1[CH2:49][O:51]1)[CH2:52][C:53]1[CH:58]=[C:57]([F:59])[CH:56]=[C:55]([O:60][CH2:61][C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH:54]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 516875Potassium PermanganateHCID 5363146Diisopropyl azodicarboxylateHCID 11443343HCID 11443343, compound

Product 1

HCID 11420189{[2-(3-Benzyloxy-5-fluoro-phenyl)-1-oxiranyl-ethylcarbamoyl]-methyl}-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In flame-dried glassware is prepared a solution of triphenylphosphine (0.291 g, 1.11 mmol, 1.10 eq.), diisopropylazodicarboxylate (0.22 mL, 1.11 mmol, 1.10 eq.) in anh. chloroform (2.5 mL). The product of Step 1 is added (0.500 g, 1.01 mmol, 1.00 eq.) with stirring under N2 overnight. The reaction is (complete as monitored by TLC; 35% EtOAc/Hexanes, KMnO4 stain) concentrated in vacuo to yield crude products as an amber oil. Calculate mass for C27H27FN2O5: 478.19. Mass found for C27H27FN2O5: (LCMS) ES+: 478.8 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customto yield crude products as an amber oil

Sources & evidence

ORD record
ord-56072beeafd9429194777b325edb9355
Source dataset
uspto-grants-2008_10
Patent number
US07442691B2

Reaction notes

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