Triethylamine → (S)-tert-Butyl 2-((S)-1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate

HRID 600304Notes

Reaction equation

HRID 600304 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:8]=[N:9][C:10]([Br:13])=[CH:11][CH:12]=1)[C:3]([NH2:5])=[O:4].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[C:27](O)=[O:28])=[O:20])([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[NH2:5][C:3](=[O:4])[C@@H:2]([NH:1][C:27]([C@@H:22]1[CH2:23][CH2:24][CH2:25][CH2:26][N:21]1[C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])=[O:28])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([Br:13])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 57999679(S)-2-Amino-3-(6-bromopyridin-3-yl)propanamide

Product 1

HCID 57999667(S)-tert-Butyl 2-((S)-1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylateYield 93.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-Amino-3-(6-bromopyridin-3-yl)propanamide (1 g), (S)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (0.939 g) and triethylamine (2.86 mL) in DMF (3 mL) were stirred under nitrogen at 0° C. 2,4,6-Tripropyl-1,3,5,2,4,6-trioxatriphosorinan-2,4,6-trioxide (3.13 g) was added and stirring at 0° C. was continued for 1 h. The reaction mixture was allowed to reach RT then it was diluted with ethyl acetate, washed with water and brine sequentially, dried over magnesium sulfate, filtered and concentrated in vacuo to give the sub-title compound (1.740 g).

Workup

  1. customto reach RT
  2. washwashed with water and brine sequentially
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6433ee9e3564424c9dd308ebe41d7f6f
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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