4-Methylmorpholine → HCID 86596883, compound

HRID 1171559Notes

Reaction equation

HRID 1171559 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:48][C@H:49]1[CH2:53][CH2:52][N:51]([C@H:54]2[CH2:59][CH2:58][C@@H:57]([NH:60][C:61](=[O:67])[O:62][C:63]([CH3:66])([CH3:65])[CH3:64])[CH2:56][C@H:55]2[CH2:68][S:69]([CH3:72])(=[O:71])=[O:70])[C:50]1=[O:73]>CN(C=O)C>[CH3:72][S:69]([CH2:68][C@H:55]1[C@@H:54]([N:51]2[CH2:52][CH2:53][C@H:49]([NH:48][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:1])([F:13])[F:12])[CH:4]=3)[C:50]2=[O:73])[CH2:59][CH2:58][C@@H:57]([NH:60][C:61](=[O:67])[O:62][C:63]([CH3:65])([CH3:64])[CH3:66])[CH2:56]1)(=[O:71])=[O:70]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 99633-(Trifluoromethyl)benzoic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86596882HCID 86596882, compound

Product 1

HCID 86596883HCID 86596883, compoundYield 129.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(Trifluoromethyl)benzoic acid (252.4 mg) was dissolved in DMF (5 mL) and 4-methyl morpholine (0.42 mL) was added prior to the addition of BOP (511 mg). After 10 min, tert-butyl (1R,3R,4S)-4-((S)-3-amino-2-oxopyrrolidin-1-yl)-3-(methylsulfonylmethyl)cyclohexylcarbamate (300 mg) was added. The reaction was stirred for 1 h before it was partitioned between EtOAc and 1N HCl solution. The organic phases were combined, washed with saturated NaHCO3 and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford tert-butyl (1R,3R,4S)-3-(methylsulfonylmethyl)-4-((S)-2-oxo-3-(3-(trifluoromethyl)benzamido)pyrrolidin-1-yl)cyclohexylcarbamate (560 mg). MS found: (M+H)+=562.2.

Workup

  1. customwas partitioned between EtOAc and 1N HCl solution
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1ad172f615384a888722cdc36fb1abd6
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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