Triethylamine → HCID 178472546, compound

HRID 613835Notes

Reaction equation

HRID 613835 reaction equation
[C:1]1([CH2:11][CH:12]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[C:13](O)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.Cl.[CH2:29]([O:31][C:32](=[O:41])[C@H:33]([CH2:35][C:36]1[N:40]=[CH:39][NH:38][CH:37]=1)[NH2:34])[CH3:30].ON1C2C=CC=CC=2N=N1.CCN(CC)CC.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[NH:38]1[CH:37]=[C:36]([CH2:35][C@H:33]([NH:34][C:13](=[O:14])[CH:12]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:32]([O:31][CH2:29][CH3:30])=[O:41])[N:40]=[CH:39]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3481676HCID 3481676, compoundHCID 178472566HCID 178472566, compound

Product 1

HCID 178472546HCID 178472546, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.5 g (1.5 mmol) of bis-(1-naphthylmethyl)-acetic acid, 0.77 g (3.0 mmol) of histidine ethyl ester dihydrochloride (His-OEt·2 HCl), and 0.22 g (1.6 mmol) of 1-hydroxybenzotriazole (HOBt) in 20 mL of THF was treated with 0.85 mL (6.0 mmol) of Et3N followed by 0.33 g (1.6 mmol) of N,N'-dicyclo hexylcarbodiimide (DCC) and the solution allowed to stir at room temperature overnight. The mixture was filtered and the solvent removed under reduced pressure. The residue was taken up in EtOAc and washed with a saturated solution of NaHCO3, then with a saturated solution of NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure gave the crude product. Chromatography on silica gel, eluting with a gradient of methylene chloride (CH2Cl2) to CH2Cl2 /MeOH (96/4) gave 0.15 g of the product as a white foam. The structure was confirmed by NMR and mass spectroscopy; (m+H)+ =506.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed under reduced pressure
  3. washwashed with a saturated solution of NaHCO3
  4. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  5. customgave the crude product
  6. washChromatography on silica gel, eluting with a gradient of methylene chloride (CH2Cl2) to CH2Cl2 /MeOH (96/4)

Sources & evidence

ORD record
ord-e99207dcf528419bb620979119c4f291
Source dataset
uspto-grants-1999_12
Patent number
US06008372

Reaction notes

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