1,2-Dichloroethane → HCID 57889440, compound

HRID 1016144Notes

Reaction equation

HRID 1016144 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].[CH3:24][O:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40](O)=[O:41])[CH:35]=1)=[O:27].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:40]([C:36]3[CH:35]=[C:34]([C:29]4[C:28]([C:26]([O:25][CH3:24])=[O:27])=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:39]=[CH:38][CH:37]=3)=[O:41])[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 20100120893736-84-0HCID 57889325HCID 57889325, compound

Product 1

HCID 57889440HCID 57889440, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-2-Amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one (40 mg, 0.107 mmol), 2′-(methoxycarbonyl)biphenyl-3-carboxylic acid (33 mg, 0.128 mmol), HOBT (20 mg, 0.128 mmol), EDC (25 mg, 0.128 mmol) and triethylamine (0.030 mL, 0.213 mmol) were mixed in methylene chloride (3 mL) at 25° C. with stirring. The reaction was stirred for 20 hours then worked up by adding methylene chloride and washing 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 (3:1 to 1:1 Hexanes/EtOAc) to obtain methyl 3′-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamoyl)biphenyl-2-carboxylate (40 mg, 0.069 mmol, 65.0% yield) as a white glass. MS found: (M+H)+=577.31.

Workup

  1. stirringThe reaction was stirred for 20 hours
  2. washwashing 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 (3:1 to 1:1 Hexanes/EtOAc)

Sources & evidence

ORD record
ord-788b329ae2c94eb1be432a4d8377b5f5
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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