Dicyclohexylcarbodiimide → HCID 86625177, compound

HRID 2090070Notes

Reaction equation

HRID 2090070 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[Br:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[Br:9][CH:10]([CH3:14])[C:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 117292-Bromopropionic acidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 86625177HCID 86625177, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-hydroxysuccinimide (4.51 g, 39.22 mmol) and 2-bromopropionic acid (2.9 mL, 32.68 mmol) were dissolved in anhydrous DCM (1000 ml) in a 2000 mL round-bottomed flask under nitrogen equipped with a magnetic stirrer. The flask was then cooled to 0° C. with an ice bath before the dropwise addition of a solution of N,N′-Dicyclohexylcarbodiimide (6.70 g, 32.68 mmol) in 50 mL of anhydrous DCM. After addition, the mixture was stirred at room temperature overnight. The reaction mixture was then filtered and the solvent evaporated to give a yellow solid that was purified by flash chromatography (CC, SiO2, Et2O, Rf(ester)=0.31). Obtained 7.2 g (28.91 mmol, 74%) of product as a white solid. Melting point: 69-70° C. 1H NMR (CDCl3) δ (ppm) 1.96 (d, 3H, CH(CH3)Br, J=6.78 Hz), 2.86 (s, 4H, Hcycl), 4.61 (q, 1H, CH(CH3)Br, J=7.03 Hz). 13C NMR (CDCl3) δ (ppm) 21.67 (1C, CH(CH3)Br) 25.74 (2C, Ccycl) 34.97 (1C, CH(CH3)Br), 166.17 (1C, C═O), 168.69 (2C, Ccycl=O). IR (solid, ATR cell) ν (cm−1) 1808, 1781 (Ccycl═O), 1729 (C═O). Mass spectroscopy (+EI, m/z) 248.964. Elem. Anal. Theoretical for C7H8NO4Br: C, 33.62; H, 3.22; N, 5.60. Found: C, 33.47; H, 3.16; N, 5.46.

Workup

  1. customequipped with a magnetic stirrer
  2. additionAfter addition
  3. filtrationThe reaction mixture was then filtered
  4. customthe solvent evaporated
  5. customto give a yellow solid
  6. customthat was purified by flash chromatography (CC, SiO2, Et2O, Rf(ester)=0.31)

Sources & evidence

ORD record
ord-59c55e8fb0f54242a2ca6b5d040fb87a
Source dataset
uspto-grants-2013_05
Patent number
US08436104B2

Reaction notes

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