Water → HCID 16115266, compound

HRID 1296254Notes

Reaction equation

HRID 1296254 reaction equation
[ClH:1].[NH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][CH:11]=2)[C:6](=[O:17])[N:5]1[CH:18]([CH3:22])[C:19](O)=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.O>CN(C=O)C.C(OCC)(=O)C>[ClH:1].[CH3:19][C@H:18]1[N:5]2[C:6](=[O:17])[C:7]3[C:12]([C@@H:4]2[CH2:3][NH:2][CH2:22]1)=[CH:11][CH:10]=[CH:9][C:8]=3[C:13]([F:16])([F:15])[F:14]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2724699PyBOPHCID 68689596HCID 68689596, compound

Product 1

HCID 16115266HCID 16115266, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirring solution of 2-(1-aminomethyl-3-oxo-4-trifluoromethyl-1,3-dihydro-isoindol-2-yl)-propionic acid hydrochloride (185 mg, 0.55 mmol) and triethylamine (268 mg, 2.65 mmol) in dry DMF (10 mL) was added benzotriazol-1-yloxy-tris(pyrrolodinyl)-phosphonium hexafluorophosphate (354 mg, 0.68 mmol). The reaction was stirred for 4 h and then conc. in vacuo to a yellow oil. The oil was partioned between water and ethyl acetate. The organic layer was separated, dried over Na2SO4, and conc. in vacuo to a yellow solid. The solid was purified by radial chromatography (silica gel, EtOAc) to give 84 mg of the desired product as a white solid. MS (ESI) 285 (M+H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. customThe solid was purified by radial chromatography (silica gel, EtOAc)

Sources & evidence

ORD record
ord-4395330838a0485da5f99cfe045c380b
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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