L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 67496344, compound

HRID 1628326Notes

Reaction equation

HRID 1628326 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]([NH:18][C@H:19]([C:27](O)=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:27](=[O:28])[C@@H:19]([NH:18][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 130983796-Bromo-2,3-dihydro-1H-indole

Product 1

HCID 67496344HCID 67496344, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The 6-bromoindoline (1050 mg, 5.30 mmol), N—BOC-phenylalanine (1.41 g, 5.30 mmol), N-ethyl-N-isopropylpropan-2-amine (2.02 ml, 12.2 mmol) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (2.41 g, 6.36 mmol) (HBTU) were dissolved in DMF. The reaction mixture was stirred for 2.5 days. The reaction was diluted with water and then extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with 1M lithium chloride solution (2×70 mL) and brine (1×70 mL) and dried over magnesium sulfate. The crude product was then recrystallyzed using ethyl acetate:hexanes to give (S)-tert-butyl 1-(6-bromoindolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (1.01 g, 42.8% yield). MS ESI (pos.) m/e: 445.1 (M+H).

Workup

  1. extractionextracted with ethyl acetate (2×150 mL)
  2. washThe combined organic layers were washed with 1M lithium chloride solution (2×70 mL) and brine (1×70 mL)
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-f37cdf49a4fd4590875e4dbf683a7e76
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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