Diisopropylethylamine → HCID 11674493, compound

HRID 915992

Reaction equation

HRID 915992 reaction equation
[C:1]1([C@H:7]([CH2:11][CH3:12])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[F:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][C:57]=1[CH2:66][NH2:67]>CN(C)C=O>[F:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]([F:63])([F:64])[F:65])=[CH:58][C:57]=1[CH2:66][NH:67][C:8](=[O:10])[C@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5338392-Fluoro-5-(trifluoromethyl)benzylamineHCID 785329(S)-2-Phenylbutyric acidHCID 2724699PyBOP

Product 1

HCID 11674493HCID 11674493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-2-phenylbutanoic acid (1-d, 50 mg, 0.30 mmol, Sigma-Aldrich, Milwaukee, Wis.) and diisopropylethylamine (98 uL, 0.60 mmol) in N,N-dimethylformamide (1 mL) was treated at room temperature with benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBop, 158 mg, 0.30 mmol). After 15 min, (2-fluoro-5-(trifluoromethyl)phenyl)methanamine (1-g, 60 mg, 0.30 mmol, Synthesis, Inc., Wyndham, N.H.) was added. The reaction mixture was stirred for 3 h, partitioned between dichloromethane and 0.5N—NaOH. The aqueous layer was removed and the organic layer was washed with 0.5N—HCl. The aqueous layer was removed by filtering through a plastic frit. The organic layer was concentrated in vacuo to give the desired product (1-1); HRMS (M+1)=340.129: 1H NMR (500 MHz, CDCl3) δ7.49 (bs, 1H), 7.41 (d, 1 H, J=6.5 Hz), 7.34–7.26 (m, 5 H), 7.10 (t, 1 H, J=9.0 Hz), 5.77 (bs, 1 H), 4.47 (d, 1 H, J=3.0 Hz), 3.30 (t, 2 H, J=7.5 Hz), 2.22 (m, 1 H), 1.82 (m, 1 H), 0.89 (t, 3 H, J=7.5 Hz).

Workup

  1. custompartitioned between dichloromethane and 0.5N—NaOH
  2. customThe aqueous layer was removed
  3. washthe organic layer was washed with 0.5N—HCl
  4. customThe aqueous layer was removed
  5. filtrationby filtering through a plastic frit
  6. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-68fbf7cb0f8b4e53bb3332a74a327afa
Source dataset
uspto-grants-2007_09
Patent number
US07268153B2

Linked notes

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