1,2-Dichloroethane → HCID 59444247, compound

HRID 1888107Notes

Reaction equation

HRID 1888107 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:25]([CH3:31])([CH3:30])[CH2:26][C:27](O)=[O:28])=[O:23])([CH3:20])([CH3:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>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:27](=[O:28])[CH2:26][C:25]([NH:24][C:22](=[O:23])[O:21][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:31])[CH3:30])[CH2:10][C:9]2([CH3:14])[CH3:15])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acidHCID 18437142(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol

Product 1

HCID 59444247HCID 59444247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (prepared in a similar manner as described in International Patent Application No. WO 04/043965, 0.949 g, 3.96 mmol), 3-(tert-butoxycarbonylamino)-3-methylbutanoic acid (0.86 g, 3.96 mmol), HOBt (1.334 g, 8.71 mmol), and Hunig's base (2.074 mL, 11.88 mmol) in methylene chloride (20 mL) was treated with EDC (1.669 g, 8.71 mmol), and the reaction was allowed to stir for about 16 h at room temperature. The mixture was concentrated in vacuo, and the residue was taken up in ethyl acetate. The organic phase was washed 3× with 1M NaOH, 3× with 1M HCl, once with water, and once with brine, dried over sodium sulfate, and concentrated in vacuo to yield an amber solid which was used as-is in the next step.

Workup

  1. customprepared in a similar manner
  2. concentrationThe mixture was concentrated in vacuo
  3. washThe organic phase was washed 3× with 1M NaOH, 3× with 1M HCl
  4. dry with materialonce with water, and once with brine, dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto yield an amber solid which

Sources & evidence

ORD record
ord-2bf53680ca414e57b1df99dbd699e089
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

Loading…