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

HRID 271980

Reaction equation

HRID 271980 reaction equation
C(C1C=CC(C([NH:11][C@H:12]([C:20]2[NH:21][CH:22]=[C:23]([C:25]3[CH:33]=[CH:32][C:28]([C:29]([NH2:31])=[O:30])=[CH:27][CH:26]=3)[N:24]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=C)=C(NCC)C=1)#N.C(C1C(NCC)=C(C=CC=1)C(O)=O)#N.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N[C@H](C(O)=O)CC1C=CC=CC=1)(OC(C)(C)C)=O.BrCC(C1C=CC(C#N)=CC=1)=O>C1COCC1.CCN(CC)CC>[NH2:11][C@H:12]([C:20]1[NH:21][CH:22]=[C:23]([C:25]2[CH:26]=[CH:27][C:28]([C:29]([NH2:31])=[O:30])=[CH:32][CH:33]=2)[N:24]=1)[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 986544-(Bromoacetyl)benzonitrileHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66674956Cyano-2-(ethylamino)benzoic acidHCID 178464543HCID 178464543, compound

Product 1

HCID 178513610HCID 178513610, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Part D: (S)-4-(2-(1-(1-(4-Cyano-2-(ethylamino)phenyl)vinylamino)-2-phenylethyl)-1H-imidazol-4-yl)benzamide: 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-4f3ec29e85cb4fe5978e0b1dc93fb0fb
Source dataset
uspto-grants-2008_11
Patent number
US07453002B2

Linked notes

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