Ethyl Acetate → HCID 178487805, compound

HRID 633805Notes

Reaction equation

HRID 633805 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18](=[O:43])[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([CH2:26][CH:27]([OH:42])[CH2:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[C:36]([O:39][CH3:40])[N:37]=3)[N:32]=[CH:31][C:30]=2O)[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:43])[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([CH2:26][CH:27]2[CH2:28][C:29]3=[C:38]4[C:33](=[N:32][CH:31]=[C:30]3[O:42]2)[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[N:37]4)[CH2:22][CH2:21]1)([CH3:14])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178487969HCID 178487969, compound

Product 1

HCID 178487805HCID 178487805, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (650 μL, 4.13 mmol, 2.0 eq) is added at 0° C. to a stirred solution of {trans-4-[2-hydroxy-3-(3-hydroxy-6-methoxy-[1,5]naphthyridin-4-yl)-propyl]-cyclohexyl}-carbamic acid tert-butyl ester (890 mg, 2.06 mmol, 1.0 eq) in tetrahydrofuran (100 mL), followed by triphenylphosphine (1.08 g, 4.13 mmol, 2.0 eq). After 1 hour 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-(8-methoxy-1,2-dihydro-3-oxa-5,9-diaza-cyclopenta[a]naphthalen-2-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester as a white solid (420 mg, 49% yield).

Workup

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

Sources & evidence

ORD record
ord-0fa9913832d342e1a56eb78de5f83489
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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