Diisopropylethylamine → (S)-tert-butyl 1-(2-(cyclopropylamino)-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate

HRID 2036593Notes

Reaction equation

HRID 2036593 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]([NH2:12])=[CH:7][CH:8]=[CH:9][C:10]=2[F:11])[CH2:3][CH2:2]1.[NH:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:14]([C:16](O)=[O:17])[CH3:15].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C2=CC=CC=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH:1]1([NH:4][C:5]2[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:16](=[O:17])[C@@H:14]([NH:13][C:19](=[O:20])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH3:15])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 2724699PyBOPHCID 58459112N1-cyclopropyl-6-fluorobenzene-1,2-diamine

Product 1

HCID 58459185(S)-tert-butyl 1-(2-(cyclopropylamino)-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N1-cyclopropyl-6-fluorobenzene-1,2-diamine (392.7 mg, 2.363 mmol) in DMF (3 mL) was added Boc-L-Ala-OH (447 mg, 2.363 mmol), 1,1′-dimethyltriethylamine (822 μL, 4.73 mmol) and (1H-benzo[d][1,2,3]triazol-1-yloxy)tripyrrolidin-1-ylphosphonium hexafluorophosphate(V) (1.23 mg, 2.36 mmol) and the resulting mixture was stirred at rt for 4 h. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel column using EtOAc:DCM (1:1) as eluent to give (S)-tert-butyl 1-(2-(cyclopropylamino)-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate: LC-MS (ESI) m/z 338.2 [M+H]+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-2b6a00cc68b144d69ed1bbf150d04830
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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