Triethylamine → HCID 59475009, compound

HRID 42551Notes

Reaction equation

HRID 42551 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([NH:24][C@H:25]1[CH2:28][CH2:27][C@H:26]1[C:29](O)=[O:30])=[O:23])([CH3:20])([CH3:19])[CH3:18].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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][N:11]([C:29]([C@H:26]3[CH2:27][CH2:28][C@H:25]3[NH:24][C:22](=[O:23])[O:21][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:30])[CH2:10][C:9]2([CH3:14])[CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18437142(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-olHCID 68495906(1R,2S)-2-{[(tert-butoxy)carbonyl]amino}cyclobutane-1-carboxylic acid

Product 1

HCID 59475009HCID 59475009, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (91 mg, 0.381 mmol), (±)-(cis)-2-(tert-butoxycarbonylamino)cyclobutanecarboxylic acid (82 mg, 0.381 mmol), and triethylamine (0.186 mL, 1.333 mmol) in methylene chloride (5 mL) was treated with BOP (168 mg, 0.381 mmol), and the mixture was stirred overnight at room temperature. At the conclusion of this period, the solvent was evaporated with a stream of nitrogen, and the resulting residue was taken up in ethyl acetate. The resulting mixture was washed 3× with saturated sodium carbonate, 3× with 1 N HCl, once with water, and once with brine, then the organic phase was concentrated in vacuo to yield the title compound (160 mg, 96% yield) as a colorless glass. The material was used as-is without further purification. MS (ESI+)=437.4 (M+H)+.

Workup

  1. customAt the conclusion of this period, the solvent was evaporated with a stream of nitrogen
  2. washThe resulting mixture was washed 3× with saturated sodium carbonate, 3× with 1 N HCl
  3. concentrationonce with water, and once with brine, then the organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-08f1dd65681040e4a09cb0d057b36abd
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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