tert-Butanol → Methyl 6-[(tert-butoxycarbonyl)amino]-2-naphthoate

HRID 2238398

反応式

HRID 2238398 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10](C(O)=O)[CH:9]=[CH:8]2)=[O:4].CC[N:20](CC)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[C:42]([O-:45])(O)=[O:43].[Na+].[CH3:47][C:48](O)([CH3:50])[CH3:49]>>[C:48]([O:45][C:42]([NH:20][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:14]=[CH:13]2)=[O:43])([CH3:50])([CH3:49])[CH3:47]

参加物

6

反応物 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 33802176-(Methoxycarbonyl)naphthalene-2-carboxylic acid

生成物 1

HCID 44549532Methyl 6-[(tert-butoxycarbonyl)amino]-2-naphthoate収率 78%

実験手順

A suspension of 6-(methoxycarbonyl)-2-naphthoic acid [J. Med. Chem., 2004, 47, 303-324] (146) (1.21 g, 5.26 mmol) in dry t-BuOH (20 mL) containing powdered molecular sieves (1 g) was treated with Et3N (0.88 mL, 6.31 mmol) and stud under N2 at room temperature for 30 min. DPPA (1.25 mL, 5.80 mmol) was added and the mixture was sired at reflux for 7 h, then cooled and poured into dilute aqueous NaHCO3. The resting solid was purified by chromatography on silica gel, eluting with CH2Cl2, followed by trituration with iPr2O and recrystallization from EtOAc to give methyl 6-[(tert-butoxycarbonyl)amino]-2-naphthoate (147) (1.24 g, 78%) as a white solid: mp 178-180° C.; 1H NMR [(CD3)2SO] δ 9.76 (s, 1H), 8.51 (s, 1H), 8.19 (s, 1H), 8.02 (d, J=9.0 Hz, 1H), 7.90 (dd, J=8.6, 1.6 Hz, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.59 (dd, J=8.9, 2.1 Hz, 1H), 3.89 (s, 3H), 1.52 (s, 9H). Anal. (C17H19NO4) C, H, N.

後処理

  1. additioncontaining
  2. temperatureat reflux for 7 h
  3. temperaturecooled
  4. customThe resting solid was purified by chromatography on silica gel
  5. washeluting with CH2Cl2
  6. customfollowed by trituration with iPr2O and recrystallization from EtOAc

出典と根拠

ORDレコード
ord-bd1c72b315d944a6b7df28551dc9fefd
出典データセット
uspto-grants-2010_05
特許番号
US07718688B2

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