Ammonia → HCID 9887247, compound

HRID 1276178Notes

Reaction equation

HRID 1276178 reaction equation
N.C([O:5][C:6]1[CH:33]=[CH:32][C:9]2[N:10]=[C:11]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]3[C:19]([NH:21][CH2:22][CH2:23][N:24]3[C@H:29]([CH3:30])[CH2:28][CH2:27][CH2:26][C@@H:25]3[CH3:31])=[O:20])[O:12][C:8]=2[CH:7]=1)(=O)C>CC(C)=O>[NH3:10].[CH3:30][C@H:29]1[CH2:28][CH2:27][CH2:26][C@@H:25]([CH3:31])[N:24]1[CH2:23][CH2:22][NH:21][C:19]([C@@H:14]1[CH2:15][CH2:16][CH2:17][CH2:18][N:13]1[C:11]1[O:12][C:8]2[CH:7]=[C:6]([OH:5])[CH:33]=[CH:32][C:9]=2[N:10]=1)=[O:20]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 12096149HCID 12096149, compound

Product 2

HCID 222AmmoniaHCID 9887247HCID 9887247, compoundYield 113.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2N Aqueous ammonia solution (10 ml) and acetone (20 ml) were added to 2-[(2S)-2-[(2-[(cis)-2,6-dimethyl-1-piperidinyl]ethylamino)carbonyl]-1-piperidinyl]-1,3-benzoxazol-6-yl acetate (0.389 g) [see Preparation 38] at 0° C. The reaction mixture was then left in a refrigerator for 18 hours, after which time the solvent was removed under reduced pressure. The remaining aqueous layer was washed twice with ethyl acetate, the combined organic layers were then dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 99:1.75:0.25 changing to 97:3.5:0.5, by volume, dichloromethane:methanol:0.88 aqueous ammonia solution to afford (2S)-N-2-[(cis)-2,6-dimethyl-1-piperidinyl]ethyl-1-(6-hydroxy-1,3-benzoxazol-2-yl)-2-piperidinecarboxamide (0.2 g) as a white foam.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. washThe remaining aqueous layer was washed twice with ethyl acetate
  3. dry with materialthe combined organic layers were then dried over magnesium sulphate
  4. customthe solvent removed under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 99:1.75:0.25 changing to 97:3.5:0.5, by volume, dichloromethane

Sources & evidence

ORD record
ord-f5e056a939b549769426536c2b68e9b8
Source dataset
uspto-grants-2000_12
Patent number
US06166011

Reaction notes

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