Acetic Anhydride → HCID 86708495, compound

HRID 921644Notes

Reaction equation

HRID 921644 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([N:18]2[CH2:23][CH2:22][C@@H:21]([NH2:24])[C@H:20]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:19]2)[C:16]=1[Cl:17])[C:12]#[N:13]>ClCCl>[NH2:8][C:9]1[C:16]([Cl:17])=[C:15]([N:18]2[CH2:23][CH2:22][C@@H:21]([NH:24][C:5](=[O:7])[CH3:6])[C@H:20]([O:25][Si:26]([C:29]([CH3:31])([CH3:30])[CH3:32])([CH3:27])[CH3:28])[CH2:19]2)[CH:14]=[C:11]([C:12]#[N:13])[CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86708496HCID 86708496, compound

Product 1

HCID 86708495HCID 86708495, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.011 mL, 0.119 mmol) was added to a solution of (+/−)-3-amino-5-((3R,4R)-4-amino-3-((tert-butyldimethylsilyl)oxy)piperidin-1-yl)-4-chlorobenzonitrile (Example 171D), (41 mg, 0.108 mmol) in dichloromethane (5 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 h. Solvent was evaporated and the crude product was purified by flash chromatography on silica gel using an automated ISCO system (24 g column, eluting with 0.5-5% methanol/dichloromethane). (+/−)-N-((3R,4R)-1-(3-amino-2-chloro-5-cyanophenyl)-3-((tert-butyldimethylsilyl)oxy)piperidin-4-yl)acetamide (44 mg) was obtained as a colorless oil which solidified upon standing.

Workup

  1. customSolvent was evaporated
  2. customthe crude product was purified by flash chromatography on silica gel using
  3. washan automated ISCO system (24 g column, eluting with 0.5-5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-1ce918ced92043948cfaac24c69fe841
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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