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

HRID 260016

Reaction equation

HRID 260016 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, 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=0), 169 (Cl).

Workup

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

Sources & evidence

ORD record
ord-39031879a7b44387af5620595a7ae9a0
Source dataset
uspto-grants-1996_06
Patent number
US05525465

Linked notes

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