Phthalic Anhydride → HCID 178447085, compound

HRID 1197936Notes

Reaction equation

HRID 1197936 reaction equation
Cl.[NH2:2][CH2:3][C@H:4]([OH:41])[C@@H:5]([NH:13][C:14](=[O:40])[C@@H:15]([NH:22][C:23](=[O:39])[C@@H:24]([CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:16][C:17]1[N:18]=[CH:19][NH:20][CH:21]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C:42]1(=O)[O:47][C:45](=[O:46])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12>C(#N)C>[CH:7]1([CH2:6][C@H:5]([NH:13][C:14](=[O:40])[C@@H:15]([NH:22][C:23](=[O:39])[C@@H:24]([CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:35])[CH3:36])[CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:16][C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[C@@H:4]([OH:41])[CH2:3][N:2]2[C:45](=[O:46])[C:44]3=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]3[C:42]2=[O:47])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 178447086HCID 178447086, compound

Product 1

HCID 178447085HCID 178447085, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

50 mg (0.08 mmol) of (S)-N-[(1S,2S)-3-amino-1-(cyclohexylmethyl)-2-hydroxypropyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]imidazole-4-propionamide hydrochloride and 1.5 g (10 mmol) of phthalic anhydride were suspended in 15 ml of acetonitrile and heated to reflux overnight. Thereafter, the reaction mixture was evaporated to dryness under reduced pressure and the residue was chromatographed on 10 g of silica gel with a mixture of methylene chloride, methanol and ammonia as the eluting agent, whereby there were obtained 31 mg of (S)-N[(1S,2S)-1-(cyclohexylmethyl)-2-hydroxy-3-phthalimidopropyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]imidazole-4-propionamide as a foam, MS: 684 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThereafter, the reaction mixture was evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed on 10 g of silica gel with a mixture of methylene chloride, methanol and ammonia as the eluting agent

Sources & evidence

ORD record
ord-709dc85d40af4b45a6a5482e581edd60
Source dataset
uspto-grants-1994_01
Patent number
US05278148

Reaction notes

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