HCID 89825014, compound → HCID 71580336, compound

HRID 2273857Notes

Reaction equation

HRID 2273857 reaction equation
C(N[C:6](=O)[N:7]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])(C)(C)C.[CH:22]1[CH:23]=[CH:24][NH+]=[CH:26][CH:27]=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH:15]1([N:7]([CH:6]2[CH2:24][CH2:23][CH2:22][CH2:27][CH2:26]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 89825014HCID 89825014, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 71580336HCID 71580336, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of silica gel (432 mg) in methylene chloride (10 mL) at room temperature was added 3-(tert-butyl)-1-cyclohexyl-1-(6-hydroxyhexyl)urea (400 mg, 1.34 mmol) and PCC (432 mg, 2.0 mmol). The mixture was stirred at this temperature for 2 hours, and then filtered through a pad of celite. The filtrate was concentrated and purified on silica gel column with a gradient of ethyl acetate in hexanes from 0:1 to 2:8 provided the product as a clear oil (190 mg, 48%). 1H NMR (300 MHz, CDCl3): δ 9.78 (t, J=1.8 Hz, 1H), 4.16 (s, 1H), 3.86-3.50 (m, 1H), 3.00 (t, J=7.9 Hz, 2H), 2.46 (td, J=7.3, 1.8 Hz, 2H), 1.87-1.46 (m, 9H), 1.46-1.20 (m, 15H), 1.20-0.95 (s, 1H).

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. custompurified on silica gel column with a gradient of ethyl acetate in hexanes from 0:1 to 2:8

Sources & evidence

ORD record
ord-b2b310456b814c07a18ab98ad97de61c
Source dataset
uspto-grants-2015_09
Patent number
US09126937B2

Reaction notes

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