Pyrrolidine → HCID 69287228, compound

HRID 2225290Notes

Reaction equation

HRID 2225290 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][C@H:13]1[C:26]([OH:28])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:40]=[CH:41][CH:42]=[N:43][C:38]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCC1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:14][C@H:13]1[C:26]([N:43]1[CH2:42][CH2:41][CH2:40][CH2:38]1)=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69285545HCID 69285545, compound

Product 1

HCID 69287228HCID 69287228, compoundYield 71.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,2S,5R)-2-benzyloxycarbonylamino-5-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (240 mg, 0.6 mmol) in DMF (15 mL) at rt was added HATU (278 mg, 0.73 mmol), pyrrolidine (0.06 mL, 0.73 mmol), and iPr2NEt (0.13 mL, 0.73 mmol). The mixture was stirred at rt for 16 h before water and EtOAc were added. The organic layer was separated and re-washed twice before it was collected, dried over Na2SO4, and concentrated to provide (1S,2R,4R)-[4-tert-butoxycarbonylamino-2-(pyrrolidine-1-carbonyl)-cyclohexyl]-carbamic acid benzyl ester as a glassy solid (190 mg, 69%). MS found: (M+H)+=446.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. washre-washed twice before it
  4. customwas collected
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-56b043036d514aaf829a9614a162f8ce
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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