Nitrogen → HCID 178520494, compound

HRID 383606Notes

Reaction equation

N#N.C[O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:29])[CH2:15][CH2:16][C:17]2[CH:22]=[C:21]([O:23]C)[C:20]([O:25]C)=[C:19]([O:27]C)[CH:18]=2)[CH2:9][CH2:8]1)=[O:6].B(Br)(Br)Br.O>C(Cl)Cl.CO>[OH:23][C:21]1[CH:22]=[C:17]([CH2:16][CH2:15][C:14]([NH:13][C@@H:10]2[CH2:11][CH2:12][C@H:7]([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]2)=[O:29])[CH:18]=[C:19]([OH:27])[C:20]=1[OH:25]

Participants

Conditions

Temperature: -78 °C

Procedure

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve cis-{4-[3-(3,4,5-Trimethoxy-phenyl)-propionylamino]-cyclohexanecarboxylic acid methyl ester (75) (82 mg, 0.21 mmol) in anhydrous DCM (2.0 mL), cool the solution to −78° C. and add dropwise BBr3 (205 μL, 2.17 mmol). Stir the reaction mixture for 20 min at −78° C. and after slowly warming up for additional 2 h at rt Add dropwise water, followed by DCM and MeOH and remove solvent. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain cis-4-[3-(3,4,5-Trihydroxy-phenyl)-propionylamino]-cyclohexanecarboxylic acid (76) (7 mg, 10%) as a colorless sticky solid. 1H NMR (400 MHz, CD3OD): 1.47-1.60 (m, 2H); 1.62-1.73 (m, 4H); 1.91-2.02 (m, 2H); 2.42 (t, 2H, J=7.6 Hz); 2.47-2.54 (m, 1H); 2.71 (t, 2H, J=7.3 Hz); 3.75-3.84 (m, 1H); 6.23 (s, 2H).

Workup

custom(The following reaction
temperatureafter slowly warming up for additional 2 h at rt
customremove solvent
customPurify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95)

Sources & evidence

ORD record: ord-d5060bca3b954da488867414e7e809a2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367677B2

Reaction notes

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