Tert-Butylamine → HCID 53835888, compound

HRID 2230288Notes

Reaction equation

HRID 2230288 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:7])([CH3:4])[CH3:3].[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24].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>CCOC(C)=O.CN(C=O)C>[C:2]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:20](=[O:22])[NH:27][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[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 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Product 1

HCID 53835888HCID 53835888, compoundYield 966.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture of BOC-L-4-nitrophenylalanine (4.65 g, 1.5 mmol), tert-butylamine (2.19 g, 30 mmol), DMF (10 mL), HBTU (5.69 g, 15 mmol), and diisopropylethylamine (2.48 g, 22 mmol) was stirred for 2 hours. After the reaction was finished, the reaction mixture was added EtOAc (75 mL), and the EtOAc solution was washed with NaHCO3 (100 mL, 4 times), dried over NaHCO3, and concentrated to dryness. The crude reaction mixture was further purified by column chromatography (SiO2, EtOAc/hexane 1:1) to yield the title compound (5.3 g), mp=158-159° C.

Workup

  1. washthe EtOAc solution was washed with NaHCO3 (100 mL, 4 times)
  2. dry with materialdried over NaHCO3
  3. concentrationconcentrated to dryness
  4. customThe crude reaction mixture
  5. customwas further purified by column chromatography (SiO2, EtOAc/hexane 1:1)

Sources & evidence

ORD record
ord-a3e6442f77834e1085dd6b51dbb9ff8c
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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