4-Methylmorpholine → HCID 66842980, compound

HRID 254079Notes

Reaction equation

HRID 254079 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[O:16])[C@H:9]2[C:24]2[CH:38]=[CH:37][C:27]([O:28][CH2:29][C:30]([NH:32]CC(O)=O)=[O:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.CN1CC[O:43][CH2:42][CH2:41]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:68][C:69]([CH3:81])([CH3:80])[CH2:70][C@@H:71]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[NH2:72].OS([O-])(=O)=O.[K+]>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)=[O:16])[C@H:9]2[C:24]2[CH:38]=[CH:37][C:27]([O:28][CH2:29][C:30]([NH:32][CH2:41][C:42]([NH:72][C@H:71]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH2:70][C:69]([CH3:81])([CH3:80])[CH3:68])=[O:43])=[O:31])=[CH:26][CH:25]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 516920Potassium bisulfateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 54211560tert-Butyl (S)-2-amino-4,4-dimethylpentanoate2×HCID 66842760N-{[4-((2R,3R)-1-(4-Fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio)-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine

Product 1

HCID 66842980HCID 66842980, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-{[4-((2R,3R)-1-(4-Fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine (20 mg, 0.037 mmol) was dissolved in 3 ml DCM. N-Methylmorpholine (9 μl, 0.082 mmol) and TBTU (14 mg, 0.044 mmol) were added. After 5 minutes, tert-butyl 4-methylleucinate (9 mg, 0.045 mmol) was added and the mixture was stirred for 2 h. Additional tert-butyl 4-methylleucinate (ca 3 mg, 0.015 mmol) was added. After 15 min, water (2 ml) was added and the mixture was acidified to a pH of 2 using 2M KHSO4. The aqueous phase was extracted with 2 ml DCM and the combined organic phases were washed with 3 ml water, dried over Na2SO4 and filtered. Removal of the solvent under reduced pressure gave the title compound. M/z: 724.

Workup

  1. waitAfter 15 min
  2. extractionThe aqueous phase was extracted with 2 ml DCM
  3. washthe combined organic phases were washed with 3 ml water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-de50dcb8c6a147c296868fc7b1bb5949
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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