Triethylamine → cis-Tert-butyl 4-(benzyloxycarbonylamino)-3-((2-(trimethylsilyl)ethoxy)-carbonylamino)piperidine-1-carboxylate

HRID 56419ノート

反応式

HRID 56419 の反応式
[NH2:1][C@H:2]1[C@@H:7]([NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:6][CH2:5][N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3]1.[C:26](=O)([O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[O:27]N1C(=O)CCC1=O.C(N(CC)CC)C>O1CCOCC1.O.C(OCC)(=O)C>[CH2:12]([O:11][C:9]([NH:8][C@H:7]1[CH2:6][CH2:5][N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3][C@H:2]1[NH:1][C:26]([O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])=[O:27])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 69440349tert-Butyl (3R,4S)-3-amino-4-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

生成物 1

HCID 131736928cis-Tert-butyl 4-(benzyloxycarbonylamino)-3-((2-(trimethylsilyl)ethoxy)-carbonylamino)piperidine-1-carboxylate収率 83%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

A solution of cis-tert-butyl 3-amino-4-(benzyloxycarbonylamino)piperidine-1-carboxylate (3.0 g, 8.6 mmol), 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate (2.5 g, 9.5 mmol) and triethylamine in dioxane/water (40 mL, v/v=1/1) was stirred at room temperature for 4 hours. After that, the solution was diluted with ethyl acetate (200 mL), and washed by 1 M hydrochloric acid (50 mL), saturated sodium bicarbonate solution (50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4/1) to afford the title compound (3.5 g, 83%) as a white solid. MS (ES+) C24H39N3O6Si requires: 493, found: 516 [M+23]+.

後処理

  1. washwashed by 1 M hydrochloric acid (50 mL), saturated sodium bicarbonate solution (50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-b8ec96f4c4c14f89bb882e672bc12439
出典データセット
uspto-grants-2016_09
特許番号
US09434700B2

反応ノート

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