Triphenylphosphine → N,O-bisphenyloxycarbonyl-t-butyloxycarbonylamino-2-propylhydroxylamine

HRID 439412ノート

反応式

HRID 439412 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 86749470N,O-bisphenyloxycarbonyl-t-butyloxycarbonylamino-2-propylhydroxylamine収率 836.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-fc2cceba9ecc4dca8fefd09f509b12a8
出典データセット
uspto-grants-1996_05
特許番号
US05514702

反応ノート

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