Dimethylformamide → HCID 178455998, compound

HRID 1655728Notes

Reaction equation

HRID 1655728 reaction equation
C(OC(=O)[CH2:5][CH:6]([CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=O)C.[NH2:22][C@@H:23]([CH2:44][C:45]1[N:46]=[CH:47][NH:48][CH:49]=1)[C:24]([NH:26][C@@H:27]([CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[C@@H:28]([OH:36])[CH2:29][C@@H:30]([CH:33]([CH3:35])[CH3:34])[CH:31]=[CH2:32])=[O:25].C(N([CH2:55][CH3:56])CC)C.CN([C:60]([O:64]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C)C=[O:84]>C(#N)C>[CH2:55]([O:84][C:60](=[O:64])[CH:10]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH:6]([C:7](=[O:9])[NH:22][C@H:23]([C:24](=[O:25])[NH:26][C@@H:27]([CH2:37][CH:38]1[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1)[C@@H:28]([OH:36])[CH2:29][C@@H:30]([CH:33]([CH3:34])[CH3:35])[CH:31]=[CH2:32])[CH2:44][C:45]1[N:46]=[CH:47][NH:48][CH:49]=1)[CH3:5])[CH3:56]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 538675143-(RS)-(1-naphthylmethyl)succinic acid 1-ethyl esterHCID 178456019HCID 178456019, compound

Product 1

HCID 178455998HCID 178455998, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

109 mg (0.38 mmol) of 3-(RS)-(1-naphthylmethyl)succinic acid 1-ethyl ester were dissolved in 6 ml of acetonitrile and 1 ml of dimethylformamide and, after the addition of 135 mg (0.35 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide, 39 mg (0.38 mmol) of triethylamine and 144 mg (0.38 mmol) of HBTU, stirred at room temperature for 6 hours. Subsequently, the reaction solution was evaporated in a high vacuum and the residue was dissolved in 50 ml of ethyl acetate and washed 3 times with 10 ml of saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and evaporated under reduced pressure, and the residue was chromatographed on silica gel with a 95:5 mixture of methylene chloride and methanol which contained 0.1% ammonium hydroxide, to obtain 103 mg (45%) of (RS)-β-[[(S)-1-[[(1S,2S, 4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]-carbamoyl]-1-naphthylbutyric acid ethyl ester as a yellowish foam. MS: 594 (M-ethanol-water)+

Workup

  1. customSubsequently, the reaction solution was evaporated in a high vacuum
  2. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
  3. washwashed 3 times with 10 ml of saturated sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customthe residue was chromatographed on silica gel with a 95:5 mixture of methylene chloride and methanol which

Sources & evidence

ORD record
ord-61cd95a575b2477082ebc55f7a3ab5e8
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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