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

HRID 579513노트

반응식

HRID 579513 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)].

후처리

  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)

출처 및 근거

ORD 기록
ord-c7b5c4fee8504f0bb54ff0519a0cda7f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

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