tert-Butanol → Tert-butyl 6-cyano-2-naphthylcarbamate

HRID 2238392

反応式

HRID 2238392 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](C(O)=O)[CH:7]=[CH:6]2)#[N:2].CC[N:18]([CH2:21]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])=CC=1.[CH3:40][C:41]([OH:44])([CH3:43])[CH3:42]>>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([NH:18][C:21](=[O:30])[O:44][C:41]([CH3:43])([CH3:42])[CH3:40])[CH:7]=[CH:6]2)#[N:2]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 124330906-Cyanonaphthalene-2-carboxylic acid

生成物 1

HCID 44549529Tert-butyl 6-cyano-2-naphthylcarbamate収率 74%

実験手順

A suspension of 6-cyano-2-naphthoic acid [J. Med. Chem., 2004, 47, 303-324] (139) (4.62 g, 23.4 mmol) in dry t-BuOH (120 mL) containing powdered molecular sieves (2 g) was treated with Et3N (3.91 mL, 28.1 mmol) and the mixture was stirred at room temperature under N2 for 30 min. DPPA (5.55 mL, 25.8 mmol) was added, and the mixture was stirred at reflux for 6 h, then concentrated to half volume and poured into dilute aqueous NaHCO3. The resulting solid was purified by chromatography on silica gel, eluting with CH2Cl2, to give tert-butyl 6-cyano-2-naphthylcarbamate (140) (4.68 g, 74%): mp (MeOH/H2O) 135-136° C.; 1H NMR [(CD3)2SO] δ 9.85 (s, 1H), 8.42 (d, J=0.9 Hz, 1H), 8.23 (d, J=1.0H, 1H), 7.95 (d, J=8.7H, 2H), 7.68 (dd, J=8.5, 1.6 Hz, 1H), 7.64 (dd, J=9.0, 2.0 Hz, 1H), 1.52 (s, 9H). Anal. (C16H16N2O2) C, H, N.

後処理

  1. additioncontaining
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 6 h
  4. concentrationconcentrated to half volume
  5. additionpoured into dilute aqueous NaHCO3
  6. customThe resulting solid was purified by chromatography on silica gel
  7. washeluting with CH2Cl2

出典と根拠

ORDレコード
ord-3e552ca8e3894f208b57401cbecdf0ca
出典データセット
uspto-grants-2010_05
特許番号
US07718688B2

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