1,2-Dichloroethane → HCID 57888900, compound

HRID 1016151Notes

Reaction equation

HRID 1016151 reaction equation
[NH2:1][C@H:2]([CH:21]([CH3:23])[CH3:22])[C:3]([N:5]1[CH2:10][CH2:9][C@@:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)([OH:11])[C:7]([CH3:20])([CH3:19])[CH2:6]1)=[O:4].[S:24]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](O)=[O:32])(=[O:27])(=[O:26])[NH2:25].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C@@:8]2([OH:11])[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C@H:2]([NH:1][C:31](=[O:32])[C:30]3[CH:34]=[CH:35][CH:36]=[C:28]([S:24](=[O:27])(=[O:26])[NH2:25])[CH:29]=3)[CH:21]([CH3:23])[CH3:22])[CH2:6][C:7]2([CH3:19])[CH3:20])=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2293523-Sulfamoylbenzoic acidHCID 57889325HCID 57889325, compound

Product 1

HCID 57888900HCID 57888900, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-2-Amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one (200 mg, 0.533 mmol), 3-sulfamoylbenzoic acid (129 mg, 0.639 mmol), HOBT (98 mg, 0.639 mmol), EDC (123 mg, 0.639 mmol) and triethylamine (0.149 mL, 1.066 mmol) were mixed in methylene chloride (3 mL) at 25° C. with stirring. The reaction was stirred for 20 hours then washed with sat'd sodium bicarbonate. The methylene chloride layer was dried over sodium sulfate and concentrated in vacuo to give a white glass which was purified over silica gel (1:1 Hexanes/EtOAc to 100% EtOAc) to obtain N-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-3-sulfamoylbenzamide (197 mg, 0.377 mmol, 70% yield) as a white glass. MS found: (M+H)+=522.32.

Workup

  1. stirringThe reaction was stirred for 20 hours
  2. washthen washed with sat'd sodium bicarbonate
  3. dry with materialThe methylene chloride layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a white glass which
  6. customwas purified over silica gel (1:1 Hexanes/EtOAc to 100% EtOAc)

Sources & evidence

ORD record
ord-56daa31f871d4033bcf19db84936270d
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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