Acetic Anhydride → Ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)hex-5-enoate

HRID 579513ノート

反応式

HRID 579513 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]([CH2:19][OH:20])([CH2:15][CH2:16][CH:17]=[CH2:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C1C=CC=CN=1)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>ClCCl>[C:30]([O:20][CH2:19][C:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])([CH2:15][CH2:16][CH:17]=[CH2:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:32])[CH3:31]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 71579992Ethyl 2-(tert-butoxycarbonylamino)-2-(hydroxymethyl)hex-5-enoate

生成物 1

HCID 86663718Ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)hex-5-enoate収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of the ethyl 2-(tert-butoxycarbonylamino)-2-(hydroxymethyl)hex-5-enoate (10.0 g, 35 mmol) and dimethylaminopyridine (4.48 g, 35 mmol) in dichloromethane (100 mL) was treated with acetic anhydride and stirred at room temperature overnight. The solution was concentrated and the resulting residue purified using a combiflash system (89 g column, eluting with 20-50% ethyl acetate in heptanes) to give ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)hex-5-enoate (10 g, 80%). 1H NMR (CDCl3) δ 5.78-5.68 (m, 1H), 5.55 (bs, 1H), 5.03-4.93 (m, 2H), 4.73 (d, J=11.0 Hz, 1H) 4.32 (d, J=11.0 Hz, 1H,), 4.20 (q, J=7.2 Hz, 2H), 2.36 (m, 1H), 2.07-2.05 (m, 1H), 2.02 (s, 3H), 1.89-1.75 (m, 2H), 1.43 (m, 9H), 1.27 (t, J=7.2 Hz, 3H). MS found for C16H27NO6 m/z[330(M+1)].

後処理

  1. concentrationThe solution was concentrated
  2. customthe resulting residue purified
  3. washa combiflash system (89 g column, eluting with 20-50% ethyl acetate in heptanes)

出典と根拠

ORDレコード
ord-c7b5c4fee8504f0bb54ff0519a0cda7f
出典データセット
uspto-grants-2015_05
特許番号
US09040703B2

反応ノート

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