Triphenylphosphine → (R)-N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine

HRID 52193

반응식

HRID 52193 반응식
[CH3:1][C@@H:2]1O[C@H:3]1[CH2:5]O.CC1C=CC(S([O-])(=O)=O)=CC=1.[Li]CCCC.[O:23]([C:30]([NH:32][O:33][C:34]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35])=[O:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(O)(=O)C>[O:23]([C:30]([N:32]([C@@H:3]([C:2]#[CH:1])[CH3:5])[O:33][C:34]([O:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:35])=[O:31])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

8

반응물 5

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10107329N,O-Bis-(phenoxycarbonyl)-hydroxylamineHCID 131719946HCID 131719946, 화합물HCID 178418339Butyllithium

생성물 1

HCID 11099408(R)-N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (2S-trans)-3-methyloxiranemethanol 4-methylbenzenesulfonate (484 mg; 2 mmol), prepared as in step 1, in dry THF (20 ml) was treated at -70° C. to -60° C. with n-BuLi (1.6M in hexane, 7.5 ml, 12 mmol) under an atmosphere of nitrogen. Glacial acetic acid (1 ml) was added after consumption of all the rosylate (monitored by TLC). After 15 min, sodium bicarbonate (600 mg) was added and the reaction mixture was allowed to warm to room temperature. After filtration through Celite, N,O-diphenoxycarbonylhydroxylamine (550 mg, 2.00 mmol) and triphenylphosphine (786 mg, 3.00 mmol) were added to the filtrate. The resulting mixture was treated with DEAD (0.5 ml, 3.0 mmol), taking care that the reaction temperature did not rise above ambient temperature. The reaction mixture was stirred at room temperature for 16 hours and then concentrated in vacuo. The residue was purifed by chromatography on silica-gel (10% ethyl acetate/hexane) to give (R)-N,O-bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine(contaminated with phenol).

후처리

  1. customafter consumption of all the rosylate (monitored by TLC)
  2. additionsodium bicarbonate (600 mg) was added
  3. additionwere added to the filtrate
  4. customdid not rise above ambient temperature
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8acfe5972ea34b25acf7ac20ff24aeb6
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616596

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