1-Propanol → HCID 68777074, compound

HRID 2069161Notes

Reaction equation

HRID 2069161 reaction equation
[ClH:1].[C:2]([CH2:5][NH:6][C@@H:7]([C:21]([N:23]1[CH2:42][CH2:41][CH2:40][C@H:24]1[C:25]([NH:27][CH2:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C:35]([NH2:39])=[N:34][CH:33]=[CH:32]2)=[O:26])=[O:22])[CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:4])=[O:3].S(Cl)([Cl:45])=O.[CH2:47](O)[CH2:48][CH3:49]>ClCCl>[ClH:45].[ClH:1].[CH2:47]([O:3][C:2](=[O:4])[CH2:5][NH:6][C@@H:7]([C:21]([N:23]1[CH2:42][CH2:41][CH2:40][C@H:24]1[C:25]([NH:27][CH2:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C:35]([NH2:39])=[N:34][CH:33]=[CH:32]2)=[O:26])=[O:22])[CH:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:48][CH3:49]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 24386Thionyl ChlorideHCID 68776188HCID 68776188, compound

Product 1

HCID 68777074HCID 68777074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-(carboxymethyl)-β-phenyl-D-phenylalanyl-N-[(1-amino-6-isoquinolyl)methyl]-L-prolinamide hydrochloride (1B; 300 mg. 0.5 mmol) in n-propanol (5 ml) was added dropwise thionyl chloride (0.4 ml). After stirring for 3 days the solution was diluted with dichloromethane, washed with 5% aqueous sodium bicarbonate solution and evaporated to dryness. The crude product was purified by reverse phase HPLC and then converted to the hydrochloride salt by dissolving in a small amount of methanol and precipitating with 1M hydrochloric acid in diethyl ether. Following addition of further anhydrous diethyl ether the resulting precipitate was collected by filtration and dried under vacuum to give 185 mg of the title compound as a white powder.

Workup

  1. washwashed with 5% aqueous sodium bicarbonate solution
  2. customevaporated to dryness
  3. customThe crude product was purified by reverse phase HPLC
  4. dissolutionby dissolving in a small amount of methanol
  5. customprecipitating with 1M hydrochloric acid in diethyl ether
  6. additionaddition of further anhydrous diethyl ether the resulting precipitate
  7. filtrationwas collected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-0b6f16b1800747a4addd19b07faa4687
Source dataset
uspto-grants-2012_10
Patent number
US08299091B2

Reaction notes

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