L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 178513610, compound

HRID 1524872Notes

Reaction equation

HRID 1524872 reaction equation
[C:1]([C:3]1[C:4](NCC)=[C:5]([CH:9]=[CH:10][CH:11]=1)C(O)=O)#[N:2].CN([P+](O[N:26]1N=[N:33][C:28]2C=CC=C[C:27]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C([NH:49][C@H:50]([C:58](O)=O)[CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)(OC(C)(C)C)=O.BrCC(C1C=CC(C#N)=CC=1)=[O:64]>C1COCC1.CCN(CC)CC>[NH2:49][C@H:50]([C:58]1[NH:26][CH:27]=[C:28]([C:9]2[CH:10]=[CH:11][C:3]([C:1]([NH2:2])=[O:64])=[CH:4][CH:5]=2)[N:33]=1)[CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

7

Reactant 4

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 986544-(Bromoacetyl)benzonitrileHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66674956Cyano-2-(ethylamino)benzoic acid

Product 1

HCID 178513610HCID 178513610, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Cyano-2-(ethylamino)benzoic acid from Example 140 Part C (40 mg, 0.2 mmol), Bop reagent (108 mg, 0.24 mmol), and Et3N (0.28 mL) were added together with 5 mL of THF. The mixture was stirred at RT for 15 minutes and (S)-4-(2-(1-Amino-2-phenylethyl)-1H-imidazol-4-yl)benzamide (107 mg, 0.2 mmol), obtained from N-boc-(L)-phenylalanine and 4-(2-Bromo-acetyl)-benzonitrile by the sequential application of the procedures described for Example 1 Part A, Example 28 Part A and Example 1 Part B, was added. The resulting mixture was heated to reflux under N2 for 2 h. The solvent were removed. The residue was dissolved in EtOAc and washed with water and brine. It was dried over MgSO4, concentrated, and purified by ISCO flash chromatography (silica, EtOAc/hexane) to give 50 mg of the desired product. LC/MS: 479.3 (M+1)+.

Sources & evidence

ORD record
ord-49e92c05695448c2af90dd9830491901
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

Loading…