tert-Butanol → HCID 66997778, compound

HRID 2426461Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[CH2:7][N:8]1[C:17](=[O:18])[C:16]([O:19][CH3:20])=[C:15]2[C:10]([CH2:11][CH2:12][N:13]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Cl:30])[CH:24]=3)[C:14]2=[O:21])=[C:9]1C(O)=O)([CH3:4])([CH3:3])[CH3:2].C([N:37]([CH2:40]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:49])C=CC=CC=1.O1CCOCC1.[C:65]([OH:69])([CH3:68])([CH3:67])[CH3:66]>>[C:65]([O:69][C:40]([NH:37][C:9]1[N:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:34])[C:17](=[O:18])[C:16]([O:19][CH3:20])=[C:15]2[C:10]=1[CH2:11][CH2:12][N:13]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Cl:30])[CH:24]=1)[C:14]2=[O:21])=[O:49])([CH3:68])([CH3:67])[CH3:66]

Participants

Reactant 5

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 312751,4-Dioxane

HCID 199401P,P-Diphenylphosphinic azide

HCID 669968852-(2-tert-Butoxy-2-oxoethyl)-6-(3-chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid

Product 1

HCID 66997778HCID 66997778, compound

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(2-tert-butoxy-2-oxoethyl)-6-(3-chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid (0.31 g, 0.62 mmol), triethylamine (0.10 mL, 0.74 mmol), and diphenylphosphoryl azide (0.19 g, 0.69 mmol) in a mixture of anhydrous dioxane (6 mL) and anhydrous tert-butanol (6 mL) was heated at 90° C. overnight. The reaction mixture was concentrated under vacuum. The residue was subject to column chromatography on silica gel. Collection and concentration of appropriate fractions provided the title compound. ES MS M+1=566

Workup

concentrationThe reaction mixture was concentrated under vacuum
customCollection and concentration of appropriate fractions

Sources & evidence

ORD record: ord-db99c5780f3f45879db63ee99cdad588
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968564B2

Reaction notes

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