Diisopropylethylamine → HCID 54505138, compound

HRID 1952734Notes

Reaction equation

HRID 1952734 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:54]([CH2:56][CH2:57][NH:58][CH2:59][CH2:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)#[N:55]>O1CCCC1>[C:54]([CH2:56][CH2:57][N:58]([CH2:59][CH2:60][CH2:61][C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)[C:18](=[O:20])[C@H:9]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])#[N:55]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acidHCID 14791345HCID 14791345, compound

Product 1

HCID 54505138HCID 54505138, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Boc-homophenylalanine (136 mg, 0.49 mmol), diisopropylethylamine (169 μl mg, 0.97 mmol), and tetrahydrofuran (3 ml) was treated with PyBrop (248 mg, 0.63 mmol) at 0° C. (2-Cyanoethyl)-3-phenylpropylamine (109 mg, 0.58 mmol) in tetrahydro-furan (2 ml) was added dropwise and the reaction mixture was stirred overnight. The solid was filtered and rinsed with ethyl acetate, and the filtrate was concentrated and purified by chromatography to give Boc-homophenylalanine (2-cyanoethyl)-3-phenyl-propylamide. A mixture of above product (200 mg), 10% palladium-on-carbon (20 mg), and methanol (40 ml) was hydrogenated on a Parr hydrogenator (40 psi) overnight. The catalyst was removed by filtration through Celite and the filtrate was concentrated in vacuo. The residue was then treated with trifluoroacetic acid for 30 min. The solvent was removed in vacuo and product was purified by reverse phase HPLC to give white solid: 1H NMR (400 MHz, D2O) δ 1.8-2.1 (m, 6 H), 2.5-2.8 (m, 4 H), 3.0-3.3 (m, 4 H), 3.3-3.7 (m, 2 H), 4.0-4.1 (m, 1 H), and 7.3-7.5 (m, 10 H).

Workup

  1. additionwas added dropwise
  2. filtrationThe solid was filtered
  3. washrinsed with ethyl acetate
  4. concentrationthe filtrate was concentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-455ff9b2113646b29f6c660d408c0f9d
Source dataset
uspto-grants-2000_09
Patent number
US06114310

Reaction notes

Loading…