Benzyl Alcohol → HCID 15042555、化合物

HRID 249399ノート

反応式

HRID 249399 の反応式
[C:1]([C:5]([CH3:11])([CH3:10])[CH2:6]C(O)=O)([O:3][CH3:4])=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])C=CC=CC=1.C([N:31]([CH2:34]C)CC)C.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1(C)C=CC=CC=1>[CH2:36]([O:43][C:34]([NH:31][CH2:6][C:5]([CH3:11])([CH3:10])[C:1]([O:3][CH3:4])=[O:2])=[O:19])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 150395654-Methoxy-3,3-dimethyl-4-oxobutanoic acid

生成物 1

HCID 15042555HCID 15042555、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

3-Carbomethoxy-3-methylbutanoic acid [Bull. Soc. Chim. Fr., 828 (1965), 7.85 g, 0.049 mol] was reacted with diphenylphosphorylazide and triethylamine as described in Example 71. After heating the toluene solution for 1.5 h, benzyl alcohol (8 g) was added directly to the reaction mixture and heating at reflux was continued for 20 h. Work-up and purification as in Example 71 gave methyl 3-benzyloxycarbonylamino-2,2-dimethylpropionate. NMR (300 MHz, CDCl3): 1.2 (s, 6H), 3.3 (d, 2H), 3.68 (s, 3H), 5.1 (s, 2H), 5.22 (m, 1H). A sample of the methyl ester (6.21 g, 0.023 mol) was saponified with 3.1 g (0.78 mol) of NaOH in 100 mL ethanol/10 mL H2O at room temperature for 48 h. Work-up as in Example 71 gave the desired product as a liquid. NMR (300 MHz, CDCl3): 1.23 (s, 6H), 3.32 (d, 2H), 5.10 (s, 2H), 5.27 (m, 1H).

後処理

  1. temperatureheating
  2. temperatureat reflux
  3. custompurification as in Example 71

出典と根拠

ORDレコード
ord-111c8a520f254bbebda971d6d22cacbe
出典データセット
uspto-grants-1993_05
特許番号
US05214129

反応ノート

読み込み中…