Tetrahydrofuran → HCID 57889099, compound

HRID 1016133Notes

Reaction equation

HRID 1016133 reaction equation
[CH:1]1([N:6]=[C:7]=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:10][C@H:11]([CH:30]([CH3:32])[CH3:31])[C:12]([N:14]1[CH2:19][CH2:18][C@@:17]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)([OH:20])[C:16]([CH3:29])([CH3:28])[CH2:15]1)=[O:13].C1COCC1>C(N(CC)CC)C>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C@@:17]2([OH:20])[CH2:18][CH2:19][N:14]([C:12](=[O:13])[C@H:11]([NH:10][C:7]([NH:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:8])[CH:30]([CH3:32])[CH3:31])[CH2:15][C:16]2([CH3:28])[CH3:29])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 643500Cyclopentyl IsocyanateHCID 67299922HCID 67299922, compound

Product 1

HCID 57889099HCID 57889099, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A reaction tube was charged with cyclopentyl isocyanate (9 μL), (R)-2-amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride (30 mg) and THF (2 mL). Triethylamine (11 μL) was added and the reaction mixture was shaken overnight at rt. After this time, the resulting solution concentrated and purified by preparative silica gel chromatography (100% EtOAc to 20% MeOH/CH2Cl2) to provide Example 511. MS found: (M+H)+=450.2.

Workup

  1. concentrationAfter this time, the resulting solution concentrated
  2. custompurified by preparative silica gel chromatography (100% EtOAc to 20% MeOH/CH2Cl2)
  3. customto provide Example 511

Sources & evidence

ORD record
ord-48da021c59a9405186bb81d7294b1799
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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