Potassium Carbonate → HCID 178448276, compound

HRID 847320Notes

Reaction equation

HRID 847320 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C@H:5]([CH:46]([CH3:48])[CH3:47])[CH2:6][C@H:7]([OH:45])[C@@H:8]([NH:16][C:17]([C@@H:19]([NH:26][C:27]([C@@H:29]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)=[O:18])[CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.CS[C:51]([NH:53][C:54](=[O:63])[O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[NH:52].CCN(C(C)C)C(C)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:40]([O:39][C:38]([NH:37][C@H:29]([C:27]([NH:26][C@H:19]([C:17]([NH:16][C@@H:8]([CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[C@@H:7]([OH:45])[CH2:6][C@@H:5]([CH:46]([CH3:48])[CH3:47])[CH2:4][CH2:3][NH:2][C:51]([NH:53][C:54](=[O:63])[O:55][CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)=[NH:52])=[O:18])[CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)=[O:28])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:44])([CH3:43])([CH3:41])[CH3:42]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 140362141Benzyl [amino(methylsulfanyl)methylene]carbamateHCID 178448274HCID 178448274, compound

Product 1

HCID 178448276HCID 178448276, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.136 g (0.197 mmol) of t-butyl [(S)-α-[[(S)-1-[[(1S,2S,4S)-6-amino-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate hydrochloride, 0.051 g (0.2 mmol) of benzyl [(methylthio)formimidoyl]carbamate and 0.07 ml (0.34 mmol) of Hunig base in 1 ml of absolute ethanol are stirred at 70° under argon for 3 hours. Thereafter, the reaction mixture is cooled, poured into 2N potassium carbonate solution and extracted with methylene chloride. The methylene chloride extracts are dried over magnesium sulphate and evaporated under reduced pressure. Chromatography of the residue obtained on 2 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 0.131 g of benzyl [N-[(3S,5S,6S)-6-[[N-[N-(t-butoxycarbonyl)-3-phenyl-L-alanyl]-L-histidyl]amino]-7-cyclohexyl-5-hydroxy-3-isopropylheptyl]amidino]carbamate as a colourless oil, MS: 831 (M+H)+.

Workup

  1. temperatureThereafter, the reaction mixture is cooled
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride extracts are dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customChromatography of the residue obtained on 2 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent

Sources & evidence

ORD record
ord-e6ff350380b5413ab73cbabc24b11ea9
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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