Potassium Hydroxide → HCID 178525811, compound

HRID 374705Notes

Reaction equation

HRID 374705 reaction equation
C[O:2][C:3](=[O:31])[C@H:4]([CH2:25][C:26]1[N:30]=[CH:29][NH:28][CH:27]=1)[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.O.O.[Br-].[Na+].[OH-].[K+]>O1CCOCC1.C(OCC)(=O)C.C(OCC)(=O)C.C(O)C>[C:7]1([C:6]([NH:5][C@H:4]([C:3]([OH:31])=[O:2])[CH2:25][C:26]2[N:30]=[CH:29][NH:28][CH:27]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 23715229HCID 23715229, compoundHCID 178501397HCID 178501397, compound

Product 1

HCID 178525811HCID 178525811, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

40 mg of L-Nα -[(2S)-3-isopropylthio-2-(1-naphthylmethyl)propionyl]-Nim triphenylmethylhistidine methyl ester was dissolved in 0.6 ml of dioxane. 0.3 ml of a 37 mg/ml sodium bromide trihydrate aqueous solution was added thereto at room temperature. The reaction solution was stirred at room temperature for 15 minutes, and then diluted with 20 ml of ethyl acetate. The reaction solution was washed with 8 ml of water and then with 8 ml of a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The reaction solution was concentrated under reduced pressure to obtain yellow solid. This product was saponified with a solution of 0.4N potassium hydroxide in methanol/water (10/1) to obtain 40 mg of L-Nα -[(2S)-3-isopropylsulfinyl-2-(1-naphthylmethyl)propionyl]-Nim -triphenylmethylhistidine (Rf: 0.48, chloroform/methanol/33% acetic acid=10/1/0.2). This compound was condensed in the same manner as in Example 11 with (2S,3R,4S)-4-amino-5-cyclohexyl-1-morpholino-2,3-pentanediol by a usual DPPA method, further subjected to removal of a triphenylmethyl group by dichloromethane/TFA (3/4). The product was purified by silica gel column chromatography (chloroform/methanol/conc. aqueous ammonia=30/3/0.02) to obtain 20 mg of (2S,3R,4S)-4-{L-Nα -[(2S)-3-isopropylsulfinyl-2-(1-naphthylmethyl)propionyl]histidyl}amino-5-cyclohexyl-1-morpholino-2,3-pentanediol as white solid.

Workup

  1. customat room temperature
  2. washThe reaction solution was washed with 8 ml of water
  3. dry with materialwith 8 ml of a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. customto obtain yellow solid

Sources & evidence

ORD record
ord-8aa70b7934264c83b122c4c58cf0ba2d
Source dataset
uspto-grants-1996_01
Patent number
US05481036

Reaction notes

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