m-Tolyl isocyanate → HCID 54548162, compound

HRID 862048Notes

Reaction equation

HRID 862048 reaction equation
C(O[C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([CH2:31][OH:32])[CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])C1C=CC=CC=1.[CH3:33][C:34]1[CH:35]=[C:36]([N:40]=C=O)[CH:37]=[CH:38][CH:39]=1.C(Cl)(Cl)Cl.CO>C(O)C.ClCCl.O1CCCC1.[C].[Pd]>[CH3:33][C:34]1[CH:35]=[C:36]([NH:40][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([CH2:31][OH:32])[CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[CH:37]=[CH:38][CH:39]=1

Participants

8

Reactant 3

HCID 69303m-Tolyl isocyanateHCID 10836729HCID 10836729, compoundHCID 21584188Chloroform methanol

Product 1

HCID 54548162HCID 54548162, compoundYield 61.6%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of N-benzyloxycarbonyl-(L)-isoleucyl-(L)-tryptophanol (0.7 g) in ethanol (30 ml)-tetrahydrofuran (20 ml), palladium-carbon (5%, 0.5 g) was subjected catalytic hydrogenation at room temperature under 1 atmospheric pressure. After the palladium-carbon was filtered off, the filtrate was concentrated under reduced pressure to yield an oily substance. This oily substance was dissolved in dichloromethane (15 ml)-tetrahydrofuran (5 ml), and m-methylphenyl isocyanate (0.225 g) was added at 4° C. After stirring at room temperature for 1.5 hours, the reaction mixture was poured over chloroform-methanol. After the insoluble substances were filtered off, the filtrate was concentrated under reduced pressure, and the residual solid was recrystallized from dichloromethane-methanol-hexane to yield N-(3-methylphenylcarbamoyl)-(L)-isoleucyl-(L)-tryptophanol (0.43 g, 61%).

Workup

  1. customat room temperature
  2. filtrationAfter the palladium-carbon was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto yield an oily substance
  5. additionwas added at 4° C
  6. filtrationAfter the insoluble substances were filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residual solid was recrystallized from dichloromethane-methanol-hexane

Sources & evidence

ORD record
ord-e2d42659f98b417395593ad6212a407b
Source dataset
uspto-grants-1998_02
Patent number
US05716980

Reaction notes

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