Dicyclohexylcarbodiimide → Pentafluorophenyl N-tert-butoxycarbonyl-6-aminohexanoate

HRID 1489412

반응식

HRID 1489412 반응식
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:17][C:18]1[C:23](O)=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28].C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[C:4]([O:3][C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][C:23]1[C:22]([F:25])=[C:21]([F:26])[C:20]([F:27])=[C:19]([F:28])[C:18]=1[F:17])=[O:15])=[O:2])([CH3:6])([CH3:7])[CH3:5]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acid

생성물 1

HCID 3091479Pentafluorophenyl N-tert-butoxycarbonyl-6-aminohexanoate수율 94%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-Boc-6-aminohexanoic acid (4.78 g, 20.8 mmol) and pentafluorophenol (3.68 g, 20 mmol) in 50 mL of EtOAc was added DCC (4.12 g, 20 mmol). This was allowed to stir for 16 h, and was then filtered and the filtrate evaporated in vacuo to a syrup. On standing, this crystallized to give 7.46 g (94%) of the ester. Rerystallization from isopropanol/1% acetic acid gave 6.26 g of white needles, mp 81°-83° C. 1H NMR (CDCl3) δ 1.4-1.6 (m, 15H, Boc CH3 and internal CH2), 1.8 (m, 2H, CH2CH2CO2), 2.67 (5, J=7.3 Hz, 2H, CH2CO2), 3.1 (m, 2H, NHCH2), 4.5 (b, 1H, NH). 13C NMR (CDCl3) δ 24.38 (C4), 26.00 (C3), 28.39 (Boc CH3), 29.70 (C5), 33.20 (C2), 40.28 (C6), 79 (Boc C), 156 (Boc C=O), 169 (C1). Anal. Calcd for C17H20NO4F5 : C, 51.4; H, 5.1; N, 3.5. Found: C, 51.5; H, 5.0; N, 3.4.

후처리

  1. filtrationwas then filtered
  2. customthe filtrate evaporated in vacuo to a syrup
  3. customthis crystallized

출처 및 근거

ORD 기록
ord-32658d8b714645e08b44cb050dc07e41
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677440

연결된 노트

불러오는 중…