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

HRID 1838408노트

반응식

HRID 1838408 반응식
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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-915a20ccf6704d60b08d33e69fa988cc
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06673804B1

반응 노트

불러오는 중…