(S)-2-Amino-3-(4-iodophenyl)propanamide → (S)-tert-Butyl 2-((S)-1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate

HRID 600291Notes

Reaction equation

HRID 600291 reaction equation
[I:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9]([NH2:11])=[O:10])[NH2:8])=[CH:4][CH:3]=1.[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].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)C>[NH2:11][C:9](=[O:10])[C@@H:7]([NH:8][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:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 447705(S)-2-Amino-3-(4-iodophenyl)propanamideHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 57999641(S)-tert-Butyl 2-((S)-1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylateYield 83.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Iodo-(L)-phenylalaninamide (2 g), (2S)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (2.4 g) and disopropylethylamine (3 mL) were dissolved in DMF (10 mL) and to the solution was added 2-(1-H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (3.3 g). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with diethyl ether (200 mL) then washed with water (250 mL) and brine (4×250 mL). The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Crude product was purified by flash silica chromatography eluting with ethyl acetate to give the sub-title compound (2.88 g) as an oil.

Workup

  1. washthen washed with water (250 mL) and brine (4×250 mL)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customCrude product was purified by flash silica chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-84aa7d1416444224a196080bbffa17cc
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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