Acetic Anhydride → HCID 178475115, compound

HRID 2404135Notes

Reaction equation

[NH2:1][C:2](=[O:35])[CH2:3][CH2:4][N:5]([CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][C@H:25]3[CH2:30][CH2:29][C@H:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:27][CH2:26]3)[CH:20]=2)[CH:15]=1)C(=O)OC(C)(C)C.[CH3:36][C:37](OC(C)=O)=[O:38]>CC(O)=O>[C:37]([NH:1][C:2](=[O:35])[CH2:3][CH2:4][NH:5][CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][C@H:25]3[CH2:26][CH2:27][C@H:28]([C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:29][CH2:30]3)[CH:20]=2)[CH:15]=1)(=[O:38])[CH3:36]

Participants

Conditions

Temperature: 90 °C

Procedure

The mixture of tert-butyl 3-amino-3-oxopropyl((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methyl)carbamate (241 mg, 0.5 mmol) in Ac2O and AcOH (6 mL, 1:5), was stirred at 90° C. for 2 h. The reaction mixture was concentrated in vacuum and the residue was purified by chromatography with silica gel (DCM/MeOH=15/1) to give the title compound as a white solid (100 mg, yield: 50%). ESI-MS (M+H+): 425.3. HPLC: 94.82%. 1H NMR (400 MHz, CDCl3) δ: 7.70 (d, 1H), 7.68 (d, 1H), 7.49 (s, 1H), 7.21 (d, 1H), 7.17-7.14 (m, 2H), 6.50 (br, 1H), 5.49 (br, 1H), 4.71 (s, 2H), 4.24-4.30 (m, 1H), 3.71 (t, 2H), 2.57 (t, 2H), 2.27 (d, 2H), 2.18 (s, 3H), 1.89 (d, 2H), 1.48-1.42 (m, 2H), 1.09-1.20 (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=15/1)

Sources & evidence

ORD record: ord-4728e859b59647d1b74fab696731002c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802659B2

Reaction notes

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