Ethyl Acetate → HCID 178487790, compound

HRID 633821Notes

Reaction equation

HRID 633821 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18](=[O:44])[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([CH2:26][CH:27]([CH2:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([O:41][CH3:42])[CH:39]=3)[N:34]=[CH:33][C:32]=2[OH:43])[CH2:28]O)[CH2:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[C:13]([O:17][C:18](=[O:44])[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([CH2:26][CH:27]2[CH2:30][C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[C:38]([O:41][CH3:42])[CH:39]=4)[N:34]=[CH:33][C:32]=3[O:43][CH2:28]2)[CH2:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178487963HCID 178487963, compound

Product 1

HCID 178487790HCID 178487790, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (455 μL, 2.90 mmol, 3.0 eq) is added at 0° C. to a stirred solution of {trans-4-[3-hydroxy-2-(3-hydroxy-6-methoxy-quinolin-4-ylmethyl)-propyl]-cyclohexyl}-carbamic acid tert-butyl ester (430 mg, 0.97 mmol, 1.0 eq) in tetrahydrofuran (100 mL), followed by triphenylphosphine (761 mg, 2.90 mmol, 3.0 eq). After 2 hours stirring at room temperature, solvent is removed and the crude is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 5:1, v/v) to afford [trans-4-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester as an off-white solid (247 mg, 60% yield).

Workup

  1. customsolvent is removed
  2. customthe crude is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-a161a3c33b51449ea0d49d28e04f59ad
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

Loading…