Dicyclohexylcarbodiimide → HCID 54273654, compound

HRID 1584094Notes

Reaction equation

HRID 1584094 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].OC1CC(=O)NC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][C:42]=1[O:49][CH3:50]>C1COCC1.C(Cl)Cl>[C:47]([C:44]1[CH:45]=[CH:46][C:41]([CH2:40][NH:39][C:10](=[O:12])[C@@H:9]2[CH2:13][CH2:14][CH2:15][N:8]2[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])=[C:42]([O:49][CH3:50])[CH:43]=1)#[N:48]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 181836963-Hydroxypyrrolidine-2,5-dioneHCID 184240904-(AMINOMETHYL)-3-METHOXYBENZONITRILE

Product 1

HCID 54273654HCID 54273654, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

16.0 g of Boc-proline (50 mmol), dissolved in 80 ml of THF, were stirred with 5.7 g of hydroxysuccinimide and 10.2 g of DCC in methylene chloride at 0° C. for 30 min. Then 8.0 g (50 mmol) of 4-aminomethyl-3-methoxybenzenenitrile [sic] dissolved in 50 ml of THF were added dropwise at 0° C., and the mixture was stirred at room temperature for 20 h. The solid was filtered off, the filtrate was mixed with the same volume of ethyl acetate and washed with cooled 5% strength NaHSO4 solution and saturated NaCl solution. 11.5 g (65%) of product were obtained. 1H-NMR (DMSO-d6 ; δ in ppm): 8.38 (m, NH); 7.50-7.35 (m, 3H); 4.40-4.05 (m, 3H, N--CH2 --Ar/N--CH--CO); 3.87 (s, OCH3); 3.50-3.25 (m, 2H, N--CH2); 2.2.5-2.00 [sic] (m, 1H); 1.90-1.65 (m, 3H); 1.40 and 1.30 (2s; 9H)

Workup

  1. additionwere added dropwise at 0° C.
  2. filtrationThe solid was filtered off
  3. additionthe filtrate was mixed with the same volume of ethyl acetate
  4. washwashed
  5. temperaturewith cooled 5% strength NaHSO4 solution and saturated NaCl solution

Sources & evidence

ORD record
ord-85befb9b04874ab6909d205eaac6a8f0
Source dataset
uspto-grants-1999_08
Patent number
US05932567

Reaction notes

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