HCID 66926612, compound → HCID 66926715, compound

HRID 2404205Notes

Reaction equation

HRID 2404205 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH:23]3[CH2:28][CH2:27][CH:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:25][CH2:24]3)[CH:18]=2)[CH:13]=1)(C)(C)C>Cl.O1CCOCC1>[C:29]([CH:26]1[CH2:25][CH2:24][CH:23]([O:22][C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12]([CH2:11][CH2:10][NH:9][CH2:8][CH2:7][C:6]([OH:33])=[O:5])[CH:21]=[CH:20]3)[CH2:28][CH2:27]1)([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 1

HCID 66926612HCID 66926612, compound

Product 1

HCID 66926715HCID 66926715, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-{2-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-ethylamino}-propionic acid tert-butyl ester (13 mg, 0.028 mmol) in 4 M of HCl in 1,4-dioxane (0.50 mL) was stirred at room temperature overnight. After the solvent was concentrated, the crude was purified via HPLC to give white solid (7 mg, yield: 49%). ESI-MS: 398.30 (M+H)+. 1H NMR (400 MHz, MeOD) δ 7.73 (d, 1H), 7.70 (d, 1H), 7.65 (s, 1H), 7.33 (dd, 1H), 7.21 (d, 1H), 7.09 (dd, 1H), 4.31 (m, 1H), 3.41-3.31 (m, 4H), 3.14 (t, 2H), 2.74 (t, 2H), 2.25 (d, 2H), 1.89 (d, 2H), 1.40 (m, 2H), 1.24 (m, 2H), 1.10 (m, 1H), 0.90 (s, 9H).

Workup

  1. concentrationAfter the solvent was concentrated
  2. customthe crude was purified via HPLC

Sources & evidence

ORD record
ord-e0d621c4ab6c4fad901434acb4b84f33
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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