Diisopropylethylamine → HCID 86609551, compound

HRID 502406Notes

Reaction equation

HRID 502406 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O)(=[O:4])=[O:3].[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.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(N(C(C)C)C(C)C)C>C1COCC1>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:9](=[O:11])[C:8]2[CH:12]=[CH:13][CH:14]=[C:6]([O:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:7]=2)[CH2:17][CH2:18]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12682914-Amino-1-Boc-piperidineHCID 184757433-[(Methylsulfonyl)oxy]benzoic acid

Product 1

HCID 86609551HCID 86609551, compoundYield 125%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared 3-methanesulfonyloxy-benzoic acid (0.400 g, 1.85 mmol) was condensed with 4-amino-1-BOC-piperidine (0.370 g, 1 eq.) in the presence of 1.1 eq. of (benzotriazol-1-yloxy)-tris-(dimethylamino)phosphonium hexafluorophosphate (0.899 g) and 1.2 eq. of N-ethyl-diisopropylamine (0.38 ml) in 9 ml of abs. THF during one night at ambient temperature. Pouring onto crashed ice/AcOEt, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=7/3), yielded 0.920 g of the title compound as white foam, contaminated with some reagent derived impurities, but sufficiently pure for the next steps.

Workup

  1. additionPouring
  2. extractionice/AcOEt, twofold extraction with AcOEt
  3. washwashing with water
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-f46e4ddaff7a451ba5896b371e460672
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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