Triphenylphosphine → HCID 86749470, 화합물

HRID 439412

반응식

HRID 439412 반응식
[C:1]([NH:8][CH2:9][CH:10](O)[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]1([O:38][C:39]([NH:41][O:42][C:43]([O:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:44])=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:32]1([O:38][C:39]([N:41]([CH:10]([CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH3:11])[O:42][C:43]([O:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:44])=[O:40])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 9920508tert-butyl N-(2-hydroxypropyl)carbamateHCID 10107329N,O-Bis-(phenoxycarbonyl)-hydroxylamine

생성물 1

HCID 86749470HCID 86749470, 화합물수율 836.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A one liter roundbottom flask was charged with N-Boc-1-amino-2-propanol (26.42 g, 0.0151 mol), triphenylphosphine (41.4 g, 0.158 mol), and N,O-bisphenyloxycarbonylhydroxylamine (43.2 g, 0.158 mol), and dry THF (550 mL). The solution was cooled to 0° C., and diethylazodicarboxylate (24.9 mL, 0.158 mol) was added in THF (50 mL). The reaction was stirred one hour after removing the cooling bath, and concentrated under vacuum. Chromatographic purification is enhanced by adding dichloromethane (200 mL) and concentrating in vacuo twice to remove THF before column chromatography (400 g silica gel, 15% EtOAc/Hex) to provide N,O-bisphenyloxycarbonyl-t-butyloxycarbonylamino-2-propylhydroxylamine (54.4 g, 80%).

후처리

  1. customafter removing the cooling bath
  2. concentrationconcentrated under vacuum
  3. customChromatographic purification
  4. additionby adding dichloromethane (200 mL)
  5. concentrationconcentrating in vacuo twice
  6. customto remove THF before column chromatography (400 g silica gel, 15% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-fc2cceba9ecc4dca8fefd09f509b12a8
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514702

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