tert-Butanol → HCID 53722169, compound

HRID 1055260Notes

Reaction equation

HRID 1055260 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[CH3:16][C:17]([OH:20])([CH3:19])[CH3:18].[NH:21]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:22]([C:35](O)=[O:36])[CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[NH:21]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:22]([C:35]([O:20][C:17]([CH3:19])([CH3:18])[CH3:16])=[O:36])[CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 2755950Boc-dap(Z)-OH

Product 1

HCID 53722169HCID 53722169, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To an ice-cold CH2Cl2 (60 mL) solution of DCC (9.78 g, 47.34 mmol), t-BuOH (17.54 g, 0.24 mol) and DMAP (0.29 g, 2.37 mmol); a CH2Cl2 (40 mL) solution of 2 (16.00 g, 47.34 mmol) was added slowly over 20 min. Then reaction mixture was allowed to stir 1 h at 0° C. and 10 h at 20° C. Precipitated urea was then filtered off and the filtrate evaporated in vacuo. The residue was taken up in CH2Cl2, and if necessary, filtered free of any further precipitated urea. The CH2Cl2 solution was washed twice with 10% citric acid solution and with saturated NaHCO3 solution, and then dried over Na2SO4. The residue obtained after evaporation of CH2Cl2 was purified by column chromatography to obtain the product as a clear viscous oil (15.67 g, 84% yield). 1H NMR (300 MHz, CDCl3) δ7.26 (5H), 5.53 (1H), 5.45 (1H), 5.02 (2H), 4.26-4.18 (1H), 3.59-3.46 (2H), 1.38 (9H), 1.37 (9H); 13C NMR (75 MHz, CDCl3) δ 169.9, 156.8, 155.8, 136.6, 128.7, 128.3, 82.8, 80.1, 66.9, 54.7, 43.3, 28.5, 28.1; ESI-LRMS m/z 395.2 (M+H)+, 417.2 (M+Na)+.

Workup

  1. customThen reaction mixture
  2. filtrationPrecipitated urea was then filtered off
  3. customthe filtrate evaporated in vacuo
  4. filtrationif necessary, filtered free of
  5. customany further precipitated urea
  6. washThe CH2Cl2 solution was washed twice with 10% citric acid solution and with saturated NaHCO3 solution
  7. dry with materialdried over Na2SO4
  8. customThe residue obtained
  9. customafter evaporation of CH2Cl2
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5ccdf864f5884dd08d195f5bb829f84e
Source dataset
uspto-grants-2016_07
Patent number
US09394338B2

Reaction notes

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