4-tert-Butylbenzoic acid → HCID 59293265, compound

HRID 1931203Notes

Reaction equation

HRID 1931203 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:14]([N:21]1[CH2:26][CH2:25][CH2:24][C@@H:23]([NH2:27])[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:27][C@@H:23]2[CH2:24][CH2:25][CH2:26][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:22]2)=[O:11])=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 74034-tert-Butylbenzoic acidHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylate

Product 1

HCID 59293265HCID 59293265, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-t-butylbenzoic acid (1.15 g, 6.45 mmol), (R)—N-BOC-3-aminopiperadine (1.00 g, 4.99 mmol), BOP (3.42 g, 7.73 mmol), and N-methylmorpholine (2.5 mL, 22.7 mmol) in DMF (10 mL) was stirred at rt for 2 hr and then heated at 55° C. for 3 hr. It was then diluted with ethyl acetate (150 mL), washed sequentially with water (3×50 mL) and brine (50 mL), and dried over anhydrous MgSO4. Removal of solvent under vacuum provided a crude product of the titled compound, which was used in the next step without further purification.

Workup

  1. temperatureheated at 55° C. for 3 hr
  2. washwashed sequentially with water (3×50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-65fe8f0ba4ba44e7acad0a021c2efd86
Source dataset
uspto-grants-2012_05
Patent number
US08188272B2

Reaction notes

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