N-Hydroxysuccinimide → HCID 178501165, compound

HRID 2402701Notes

Reaction equation

HRID 2402701 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[CH3:9][O:10][C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19](O)=[O:20])[CH2:15][CH2:14]1)=[O:12]>C1COCC1>[O:8]=[C:3]1[CH2:4][CH2:5][C:6](=[O:7])[N:2]1[O:1][C:19]([C@H:16]1[CH2:15][CH2:14][C@H:13]([C:11]([O:10][CH3:9])=[O:12])[CH2:18][CH2:17]1)=[O:20]

Participants

4

Reactant 2

HCID 80170N-HydroxysuccinimideHCID 178501163HCID 178501163, compound

Product 1

HCID 178501165HCID 178501165, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-hydroxysuccinimide (6.18 g, 0.0537 mol) and trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (10.00 g, 0.05370 mol) in THF (100.00 mL) was charged with (N,N-dicyclohexylcarbodiimide (11.08 g, 0.0537 mol) in THF (16 mL). This reaction was stirred at rt for an additional 16 h then stirred at 45° C. for 1 h. The reaction mixture was filtered while still warm through a fitted funnel. The cake was washed with 3 more portions of THF and the filtrate was concentrated in vacuo and was crystallized from i-PrOH (300 mL) and filtered through a fritted funnel resulting in 11.8 g, (78% yield) of the title compound as a white crystals. 1H NMR (400 MHz, CDCl3) δ ppm 1.45-1.69 (m, 4H), 2.07-2.16 (m, 2H), 2.18-2.28 (m, 2H), 2.29-2.39 (m, 1H), 2.59-2.71 (m, 1H) 2.84 (br. s., 4H) and 3.68 (s, 3H); MS (ES+): m/z 284.09 [MH+].

Workup

  1. stirringthen stirred at 45° C. for 1 h
  2. filtrationThe reaction mixture was filtered
  3. temperaturewhile still warm through a fitted funnel
  4. washThe cake was washed with 3 more portions of THF
  5. concentrationthe filtrate was concentrated in vacuo
  6. customwas crystallized from i-PrOH (300 mL)
  7. filtrationfiltered through a fritted funnel

Sources & evidence

ORD record
ord-4361d9692a634f22b955ec1c77b89cb9
Source dataset
uspto-grants-2014_08
Patent number
US08796455B2

Reaction notes

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