Triethylamine → HCID 57803313, compound

HRID 2367036Notes

Reaction equation

HRID 2367036 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.[F:14][C:15]([F:32])([F:31])[C:16]1[CH:17]=[C:18]([N:22]2[CH2:27][CH2:26][CH:25]([C:28](O)=[O:29])[CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.CCOC(C)=O>[F:31][C:15]([F:14])([F:32])[C:16]1[CH:17]=[C:18]([N:22]2[CH2:27][CH2:26][CH:25]([C:28]([N:1]3[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]3)=[O:29])[CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 57803369HCID 57803369, compound

Product 1

HCID 57803313HCID 57803313, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl (3S)-pyrrolidin-3-ylcarbamate (0.65 g, 3.5 mmol), 1-[3-(trifluoromethyl)phenyl]piperidine-4-carboxylic acid (0.80 g, 2.9 mmol), triethylamine (0.82 mL, 5.8 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.4 g, 3.2 mmol) were mixed in dry methylene chloride (10 mL). After being stirred overnight, the reaction mixture was diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried (MgSO4), concentrated and flash chromatographed (20% EtOAc/hexanes to 40% EtOAc/hexanes) to give 0.975 g of the desired product. MS (M+H) 442.1.

Workup

  1. washwashed with saturated NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAc three times
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. customflash chromatographed (20% EtOAc/hexanes to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2c71b25fdcba4ebfb3cf78a611a4728a
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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