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

HRID 1456908

Reaction equation

HRID 1456908 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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, C2CH2CO2), 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=0), 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.

Workup

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

Sources & evidence

ORD record
ord-de2e1a80682d44898fff4a6c993cef4a
Source dataset
uspto-grants-1998_12
Patent number
US05846728

Linked notes

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