Triethylamine → HCID 178501411, compound

HRID 1735507Notes

Reaction equation

HRID 1735507 reaction equation
Cl.Cl.[CH3:3][O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[NH2:7].C(N(CC)CC)C.[O:22]1[CH2:27][CH2:26][N:25]([C:28]([C:30]([S:33]([CH2:36][C@@H:37]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:38](O)=[O:39])(=[O:35])=[O:34])([CH3:32])[CH3:31])=[O:29])[CH2:24][CH2:23]1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.ON1C=CC=CC1=O.C(#N)C>[CH3:3][O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[NH:7][C:38](=[O:39])[C@@H:37]([CH2:36][S:33]([C:30]([CH3:31])([C:28]([N:25]1[CH2:26][CH2:27][O:22][CH2:23][CH2:24]1)=[O:29])[CH3:32])(=[O:34])=[O:35])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 54181919HCID 54181919, compoundHCID 178419105HCID 178419105, compound

Product 1

HCID 178501411HCID 178501411, compoundYield 101%

Reagents, catalysts & solvents 3

HCID 69975HydroxypyridinoneCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

2.5 g (10.5 mmol) of histidine methyl ester dihydrochloride, 10 ml of acetonitrile and 2.9 ml (148 mmol) of triethylamine were stirred at 20° for 20 hours. 3.8 g (10 mmol) of (S)-α[[[1-(morpholinocarbonyl)-1-methylethyl]sulphonyl]methyl]hydrocinnamic acid, 0.11 g (1 mmol) of 1-hydroxy-2(1H)-pyridone and 20 ml of ethyl acetate were subsequently added. After 15 minutes a solution of 2.2 g (10.5 mmol) of dicyclohexylcarbodiimide in 15 ml of ethyl acetate was added within 30 minutes. The reaction had finished after stirring at 20° for 18 hours. The solid (dicyclohexylurea) was filtered off under suction and the filtrate was washed with aqueous sodium bicarbonate solution and water. 5.4 g of N-[(S)-α-[[[1-methyl-1-(morpholinocarbonyl)ethyl]sulphonyl]methyl]hydrocinnamoyl]-L-histidine methyl ester were obtained.

Workup

  1. filtrationThe solid (dicyclohexylurea) was filtered off under suction
  2. washthe filtrate was washed with aqueous sodium bicarbonate solution and water

Sources & evidence

ORD record
ord-e5bd1aa8f3a64f60ac536520e8986db1
Source dataset
uspto-grants-1996_07
Patent number
US05536816

Reaction notes

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