Triphenylphosphine → HCID 178501290, 화합물

HRID 1194917노트

반응식

HRID 1194917 반응식
N(C(OCC)=O)=NC(OCC)=O.[OH:13]/[N:14]=[C:15](/[C:23](=[O:25])[CH3:24])\[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].O[C@@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:19]([O:18][C:16](=[O:17])/[C:15](=[N:14]\[O:13][C@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:28]1)/[C:23](=[O:25])[CH3:24])([CH3:21])([CH3:20])[CH3:22]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178468383HCID 178468383, 화합물HCID 178501284HCID 178501284, 화합물

생성물 1

HCID 178501290HCID 178501290, 화합물수율 33.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of diethyl azodicarboxylate (1.62 ml) in tetrahydrofuran (5 ml) was added dropwise to a solution of tert-butyl (Z)-2-hydroxyimino-3-oxobutyrate (1.6 g), methyl cis-4-hydroxycyclohexanecarboxylate (1.9 g) and triphenylphosphine (2.7 g) in tetrahydrofuran (20 ml) over 15 min at room temperature. The mixture was stirred for 18h, then the solvent removed under reduced pressure. The residue was chromatographed on silica to give the title compound (0.93 g, 33%) as a colourless liquid. νmax (film) 2950, 1730, and 1690 cm-1. δH (CDCl3) 1.47-1.64 (3H, m), 1.53 (9H, s), 1.56 (3H, d, J 5.3 Hz), 2.05 (2H, m), 2.17 (2H, m), 2.35 (1H, m), 2.37 (3H, s), 3.69 (3H, s), and 4.24 (1H, tt, J 4.1, 10.0 Hz), δC (CDCl3) 25.2, 26.3 (2C), 28.1 (3C), 29.9 (2C), 41.6, 51.7, 82.9, 84.0, 160.6, 175.5, and 193.0. [Mass spectrum +ve ion (ammonia) MH+ (328), MNH4+ (345)].

후처리

  1. customthe solvent removed under reduced pressure
  2. customThe residue was chromatographed on silica

출처 및 근거

ORD 기록
ord-762f1e9a29a64a109357603fb27a61b2
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04816452

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