Ammonia → (S)-tert-Butyl 1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamate

HRID 600302Notes

Reaction equation

HRID 600302 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10](O)=[O:11])=[CH:4][CH:3]=1.C([N:23]1CCOCC1)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N>CN(C=O)C.C(OCC)(=O)C>[NH2:23][C:10](=[O:11])[C@@H:9]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:8][C:5]1[CH:6]=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7525EthylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57999631(S)-3-(6-Bromopyridin-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Product 1

HCID 57999677(S)-tert-Butyl 1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-3-(6-Bromopyridin-3-yl)-2-(tert-butoxycarbonylamino)propanoic acid (1.72 g), N-ethylmorpholine (1.261 mL) and TBTU (2.4 g) were combined in DMF (5 mL) and the solution was stirred, at room temperature for 0.5 h then it was cooled to 0° C. Aqueous 880 ammonia (0.827 mL) was added and the mixture was allowed to reach RT overnight. The reaction mixture was diluted with ethyl acetate, washed with water then brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give the sub-title compound (1.5 g).

Workup

  1. temperatureit was cooled to 0° C
  2. waitto reach RT overnight
  3. washwashed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b5874231b544230805923d6cd477922
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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