Benzyl isocyanate → HCID 131719310, compound

HRID 54163Notes

Reaction equation

HRID 54163 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:6]([NH:8][C@H:9]([C:11]([O:13][CH3:14])=[O:12])[CH3:10])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH2:25]([N:32]=[C:33]=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO.C(Cl)(Cl)Cl.[Pd]>[C:26]1([CH2:25][NH:32][C:33]([NH:1][C@H:2]([C:6]([NH:8][C@H:9]([C:11]([O:13][CH3:14])=[O:12])[CH3:10])=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 76639Benzyl isocyanateHCID 7015715Z-Val-ala-ome

Product 1

HCID 131719310HCID 131719310, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

CBZValAlaOCH3 (1.35 g, 4.00 mmole) was hydrogenated at 3 atm. over 10% Pd on carbon (150 mg) in CH3OH (40 mL) at room temperature. After 1 hour, the catalyst was removed by filtration through a nylon filter. The filtrate was evaporated in vacuo giving a white solid which was slurried in CHCl3 (40 mL) and treated with benzyl isocyanate (586 mg, 4.4 mmole). After 1 hour at room temperature, the reaction mixture was washed three times with 1N HCl, dried over MgSO4, filtered and concentrated in vacuo giving 791 mg (61%) of the desired product as a white powder. Recrystallization of a portion from ethyl acetate/CH3OH gave an analytical sample: mp 227°-228° C.; 1H NMR (DMSO-d6) δ 0.80 (d, J=6.8 Hz, 3H), 0.86 (d, J=6.7 Hz, 3H), 1.26(d, J=7.3 Hz, 3H), 1.85-1.95 (m, 1H), 3.59 (s, 3H), 4.10 (dd, J=5.9, 9.2 Hz, 1H), 4.15-4.3 (m, 3H), 6.08 (d, J=9.3 Hz, 1H), 6.53 (t, J=6.0 Hz, 1H), 7.15-7.35 (m, 5H), 8.39 (d, J=6.7 Hz, 1H); MS (LSIMS) m/e 336 (100, M+ +1), 233 (62), 203 (76); [α]D20 +6.1° (c=1.0, DMF); Analysis calculated for C17H25N3O4 ; C, 60.88; H, 7.51; N, 12.53; found: C, 60.98; H, 7.30; N, 12.34.

Workup

  1. customthe catalyst was removed by filtration through a nylon
  2. filtrationfilter
  3. customThe filtrate was evaporated in vacuo
  4. customgiving a white solid which
  5. waitAfter 1 hour at room temperature
  6. washthe reaction mixture was washed three times with 1N HCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01d4a280381f44db9e5481e1cf287713
Source dataset
uspto-grants-1997_04
Patent number
US05622830

Reaction notes

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