1-Hydroxybenzotriazole → HCID 70049354, compound

HRID 1647092Notes

Reaction equation

HRID 1647092 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:23])[CH2:21][NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:24]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([NH:35][C@H:36]([C:40]([N:42]2[CH2:59][CH2:58][CH2:57][C@H:43]2[C:44]([NH:46][CH:47]([CH:54]([CH3:56])[CH3:55])[C:48](=[O:53])[C:49]([F:52])([F:51])[F:50])=[O:45])=[O:41])[CH:37]([CH3:39])[CH3:38])=[O:34])=[CH:29][CH:28]=1)(O)=[O:25].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:12]([O:19][C:20]([CH2:21][NH:22][C:24]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([NH:35][C@H:36]([C:40]([N:42]2[CH2:59][CH2:58][CH2:57][C@H:43]2[C:44]([NH:46][CH:47]([CH:54]([CH3:55])[CH3:56])[C:48](=[O:53])[C:49]([F:50])([F:51])[F:52])=[O:45])=[O:41])[CH:37]([CH3:39])[CH3:38])=[O:34])=[CH:29][CH:28]=1)=[O:25])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 10577714HCID 10577714, compound

Product 1

HCID 70049354HCID 70049354, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of glycine benzyl ester p-toluenesulfonate (66 mg) and 3(RS)-[(4-carboxyphenylcarbonyl)-L-valyl-L-prolyl]amino-1,1,1-trifluoro-4-methyl-2-oxopentane (100 mg) in DMF (6 ml) were added HOBT (26 mg) and WSCD (30 mg) under ice-bath cooling. After being stirred at room temperature for 4 hours, the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (30 ml) and washed with 5% aqueous citric acid (20 ml), water (20 ml), 5% aqueous sodium bicarbonate (20 ml) and brine (20 ml). The solution was dried over magnesium sulfate and evaporated under reduced pressure to give 3(RS)-[[4-[(benzyloxycarbonyl)methylaminocarbonyl]phenylcarbonyl]-L-valyl-L-prolyl]amino-1,1,1-trifluoro-4-methyl-2-oxopentane (125 mg).

Workup

  1. temperaturecooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  4. washwashed with 5% aqueous citric acid (20 ml), water (20 ml), 5% aqueous sodium bicarbonate (20 ml) and brine (20 ml)
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8d27a3cfc64c44cab093f7a994d886a4
Source dataset
uspto-grants-1995_07
Patent number
US05430025

Reaction notes

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