Methyltriphenylphosphonium iodide → benzyl (S)-1-((1S,2R,4R)-4-amino-2-ethylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

HRID 1455407Notes

Reaction equation

HRID 1455407 reaction equation
[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OC(N1C(=O)[C@@H]2C[C@H]1CC[C@@H]2NC(OCC1C=CC=CC=1)=O)=O)(C)(C)C.[CH2:49]([O:56][C:57](=[O:81])[NH:58][C@H:59]1[CH2:63][CH2:62][N:61]([C@H:64]2[CH2:69][CH2:68][C@@H:67]([NH:70]C(OC(C)(C)C)=O)[CH2:66][C@H:65]2[CH2:78][CH3:79])[C:60]1=[O:80])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:70][C@@H:67]1[CH2:68][CH2:69][C@H:64]([N:61]2[CH2:62][CH2:63][C@H:59]([NH:58][C:57](=[O:81])[O:56][CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[C:60]2=[O:80])[C@H:65]([CH2:78][CH3:79])[CH2:66]1

Participants

5

Reactant 3

HCID 638159Methyltriphenylphosphonium iodideHCID 68765971HCID 68765971, compoundHCID 68767907{(3S)-1-[(1S,2R,4R)-4-tert-butoxycarbonylamino-2-ethyl-cyclohexyl]-2-oxo-pyrrolidin-3-yl}-carbamic acid benzyl ester

Product 1

HCID 86596874benzyl (S)-1-((1S,2R,4R)-4-amino-2-ethylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Following the procedures described in Example 2a, Steps 1-4, and substituting methyl triphenylphosphonium iodide in Step 1, (1R,2S,5R)-2-benzyloxycarbonylamino-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester was converted to {(3S)-1-[(1S,2R,4R)-4-tert-butoxycarbonylamino-2-ethyl-cyclohexyl]-2-oxo-pyrrolidin-3-yl}-carbamic acid benzyl ester. A portion of this material (995 mg, 2.2 mmol) was dissolved in 20 mL of 4:1 CH2Cl2/TFA. The resultant solution was stirred at RT for 3 h and concentrated in vacuo. The residue was dissolved in methylene chloride and concentrated in vacuo; this procedure was repeated twice more to afford benzyl (S)-1-((1S,2R,4R)-4-amino-2-ethylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate. MS found: (M+H)+=360.2.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80fac905ae8d4916a8aec725d09124ca
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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