Phthalimide → (+/-)-n-(Tert-butoxycarbonyl)-2-(phthalimidoethyl)glycine allyl ester

HRID 1838408ノート

反応式

HRID 1838408 の反応式
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:16][C:17](=[O:30])[C@H:18]([CH2:27][CH2:28]O)[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=[CH2:15].[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH2:13]([O:16][C:17](=[O:30])[CH:18]([CH2:27][CH2:28][N:35]1[C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]2[C:31]1=[O:41])[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=[CH2:15]

参加物

5

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12042107(+/-)-N-(tert-butoxycarbonyl)homoserine allyl ester

生成物 1

HCID 18753589(+/-)-n-(Tert-butoxycarbonyl)-2-(phthalimidoethyl)glycine allyl ester収率 73%

実験手順

Diethyl azodicarboxylate (5.7 ml, 36.2 mmol, abbreviated as DEAD hereinafter) was added dropwise to a mixture of (±)-N-(tert-butoxycarbonyl)homoserine allyl ester (7.79 g, 30.0 mmol), phthalimide (4.41 g, 30 mmol), triphenylphosphine (9.45 g, 36.0 mmol) and tetrahydrofuiran (75 ml) at room temperature with stirring. This mixture was stirred for 1 hour. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=4/1 as the eluent to afford the desired compound (8.46 g, yield 73%) as a white powder.

後処理

  1. stirringThis mixture was stirred for 1 hour
  2. customThe solvent of the reaction mixture was evaporated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-915a20ccf6704d60b08d33e69fa988cc
出典データセット
uspto-grants-2004_01
特許番号
US06673804B1

反応ノート

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