Triethylamine → HCID 178453518, compound

HRID 713914Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:25][C@H:26]3[CH2:31][CH2:30][C@H:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27]3)[CH:21]=2)[CH:16]=1)[CH2:9][CH2:10][C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+:36].[Cl-].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[NH2:36][C:11](=[O:12])[CH2:10][CH2:9][N:8]([CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:25][C@H:26]3[CH2:27][CH2:28][C@H:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:30][CH2:31]3)[CH:21]=2)[CH:16]=1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

The mixture of 3-(tert-butoxycarbonyl((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methyl)amino)propanoic acid (483 mg, 1.0 mmol), NH4Cl (215 mg, 5.0 mmol, 5.0 equiv), Et3N (510 mg, 5.0 mmol, 5.0 equiv) and HATU (760 mg, 2.0 mmol, 2.0 equiv) in anhydrous THF (20 mL) was stirred at 45° C. for 15 min. The reaction mixture was concentrated in vacuum and the residue was purified by chromatography with silica gel (DCM/MeOH=20/1) to give compound the title compound as a white solid (337 mg, yield: 70%). ESI-MS (M+H+): 483.3. 1H NMR (400 MHz, DMSO-d6) δ: 7.76 (d, 2H), 7.60 (s, 1H), 7.34 (s, 1H), 7.30 (d, 1H), 7.12 (dd, 1H) 4.49 (s, 2H), 4.38-4.31 (m, 1H), 3.30 (t, 2H), 2.30 (t, 2H), 2.19 (d, 2H), 1.81 (d, 2H), 1.45-1.33 (m, 11H), 1.23-1.16 (m, 3H), 0.88 (s, 9H).

Workup

concentrationThe reaction mixture was concentrated in vacuum
customthe residue was purified by chromatography with silica gel (DCM/MeOH=20/1)

Sources & evidence

ORD record: ord-5d8f9e669b6347cf8740fb0df5d683c1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186367B2

Reaction notes

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