1,2-Naphthoquinone → HCID 57661867, compound

HRID 1665429Notes

Reaction equation

HRID 1665429 reaction equation
[OH:1][C:2]1([CH2:16][SH:17])[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[C:18]1(=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]1=[O:28]>>[O:28]=[C:19]1[C:20]2[S:17][CH2:16][C:2]3([CH2:3][CH2:4][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:6][CH2:7]3)[O:1][C:21]=2[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]1=[O:29]

Participants

3

Reactant 2

HCID 106671,2-NaphthoquinoneHCID 86629715HCID 86629715, compound

Product 1

HCID 57661867HCID 57661867, compound

Procedure

The crude tert-butyl [4-hydroxy-4-(mercaptomethyl)cyclohexyl]carbamate was reacted with naphthalene-1,2-dione as outlined in procedure G [both step (i) (ii) and (iii)] to afford crude tert-butyl (5′,6′-dioxo-5′,6′-dihydrospiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiin]-4-yl)carbamate. The crude product was purified by flash column chromatography (SiO2, 100% dichloromethane) to afford the product as a purple solid. M.p.=224-225° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.90 (dd, J=7.6 Hz, 0.8 Hz, 1H), 7.83 (d, J=6.8 Hz, 1H), 7.75 (td, J=7.6 Hz, 1.2 Hz, 1H), 6.92 (d, J=8.4 Hz, 1H), 3.34 (br, 1H), 3.02 (s, 2H), 2.05 (d, J=10.8 Hz, 2H), 1.76-1.53 (m, 6H), 1.39 (s, 9H); LCMS: 416 [M+H].

Workup

  1. customto afford crude tert-butyl (5′,6′-dioxo-5′,6′-dihydrospiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiin]-4-yl)carbamate
  2. customThe crude product was purified by flash column chromatography (SiO2, 100% dichloromethane)

Sources & evidence

ORD record
ord-331bee4a35354fffbc86286ea55f5c2f
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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