4-Methylmorpholine → 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-phenylmethyldihydrofuran-2-(3H)one

HRID 1376657Notes

Reaction equation

HRID 1376657 reaction equation
C1(CCCC[C@H]([CH2:15][C:16]2[CH:21]=CC=C[CH:17]=2)C(O)=O)C=CC=CC=1.F[P-](F)(F)(F)(F)F.[N:29]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:33]2[CH:34]=CC=[CH:37][C:32]=2N=N1.[CH:49]1[CH:50]=[CH:51][C:52]2N(O)N=N[C:53]=2[CH:54]=1.CN1C[CH2:64][O:63]CC1.N[C@H](C(N[C@H:74]([C:82]([OH:84])=[O:83])[CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)=O)C(C)C.N1([NH-])CC[O:88]CC1>CN(C=O)C>[C:64]([NH:29][C@H:33]([C@H:32]1[O:84][C:82](=[O:83])[C@H:74]([CH2:75][C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=2)[CH2:37]1)[CH2:34][C:53]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:54]=1)([O:63][C:16]([CH3:15])([CH3:17])[CH3:21])=[O:88]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 131718982H-(L)-Val-(L)-Phe morpholin-4-ylamideHCID 1317201586-phenyl-(R)-phenylmethyl-hexanoic acid

Product 1

HCID 117320045(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-phenylmethyldihydrofuran-2-(3H)one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 250 mg of 5(S)-(Boc-amino)-4(S)-tert-butyldimethylsilyloxy)-6-phenyl-(R)-phenylmethyl-hexanoic acid in 3 ml of DMF with 230.5 mg of BOP, 70.4 mg of HOBT and 182.6 ml of N-methylmorpholine is stirred for 30 minutes at room temperature in approximately 2 ml of DMF, and then 189.5 mg of H-(L)-Val-(L)-Phe-morpholin-4-ylamide [preparation, see under 1 k) to 1 n)] are added. After 16 hours at room temperature, the reaction mixture is concentrated by evaporation and the residue is partitioned between three portions of ethyl acetate, water, saturated sodium hydrogen carbonate solution, water and brine, and the organic phases are dried with sodium sulfate and concentrated by evaporation, yielding the title compound as a crude product; TLC Rf (A)=0.24; FAB-MS (M+H)+ =843.

Workup

  1. additionare added
  2. concentrationthe reaction mixture is concentrated by evaporation
  3. customthe residue is partitioned between three portions of ethyl acetate, water, saturated sodium hydrogen carbonate solution, water and brine
  4. dry with materialthe organic phases are dried with sodium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-485351da53da449cacd5700783b48a43
Source dataset
uspto-grants-1997_09
Patent number
US05663168

Reaction notes

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