Tert-Butylamine → HCID 70060826, compound

HRID 2230291Notes

Reaction equation

HRID 2230291 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:18]([OH:20])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])[CH3:3].[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(OCC)C.CN(C=O)C>[C:2]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:18](=[O:20])[NH:25][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([I:17])=[CH:15][CH:16]=1)([CH3:1])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2755956(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

Product 1

HCID 70060826HCID 70060826, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A reaction mixture of BOC-L-4-iodophenylalanine (10 g, 25.6 mmol), tert-butylamine (2.19 g, 30 mmol), DMF (25 mL), HBTU (9.7 g, 25.6 mmol), and diisopropylethylamine (6.6 g, 51 mmol) was stirred for 2 hours. The mixture was diluted with 40 mL of diethylether, washed with 1N HCl (2×25 mL), saturated NaHCO3 (2×25 mL), and saturated solution of brine (2×25 mL). The organic layer was separated, dried with Na2SO4, and evaporated to dryness. The crude was purified by column chromatography (silica gel, 25% EtOAc/hexanes) to yield the title compound (10.2 g).

Workup

  1. washwashed with 1N HCl (2×25 mL), saturated NaHCO3 (2×25 mL), and saturated solution of brine (2×25 mL)
  2. customThe organic layer was separated
  3. dry with materialdried with Na2SO4
  4. customevaporated to dryness
  5. customThe crude was purified by column chromatography (silica gel, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b5764f21c0ff4e0abb9451b5fab9fad4
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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