1-Isocyanato-4-methoxybenzene → HCID 178492036, compound

HRID 1268970Notes

Reaction equation

HRID 1268970 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][NH:22][C@H:23]([C:35]2[NH:36][CH:37]=[C:38]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:39]=2)[CH2:24][C:25](OCC2C=CC=CC=2)=[O:26])=[CH:13]1>C1COCC1>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][N:22]2[C@H:23]([C:35]3[NH:36][CH:37]=[C:38]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[N:39]=3)[CH2:24][C:25](=[O:26])[N:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:10]2=[O:11])=[CH:13]1

Participants

4

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 178520773HCID 178520773, compound

Product 1

HCID 178492036HCID 178492036, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

4-methoxyphenylisocyanate (40 μl, 1.2 eq.) is added to a solution of benzyl (3S)-3-[(1H-indol-3-ylmethyl)amino]-3-(4-phenyl-1H-imidazol-2-yl)propanoate (100 mg, 1 eq.) in THF (2 ml). The mixture is stirred for 5 hours at a temperature of approximately 20° C. then diluted with 2 ml of THF. An aminomethylpolystyrene resin (acquired from Novabiochem, load 3.2 mmol/g, 138 mg, 2 eq.) is added. The mixture is stirred for 3 hours at a temperature of approximately 20° C. then filtered on frit. The filtrate is concentrated under reduced pressure at 40° C. 2 ml of THF and 2 ml of triethylamine are added to the residue. The mixture is taken to reflux for 24 hours then concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (eluent: ethyl acetate/heptane 8:2) yields the expected compound (80 mg, yield 74

Workup

  1. additionAn aminomethylpolystyrene resin (acquired from Novabiochem, load 3.2 mmol/g, 138 mg, 2 eq.) is added
  2. stirringThe mixture is stirred for 3 hours at a temperature of approximately 20° C.
  3. filtrationthen filtered on frit
  4. concentrationThe filtrate is concentrated under reduced pressure at 40° C
  5. addition2 ml of THF and 2 ml of triethylamine are added to the residue
  6. temperatureto reflux for 24 hours
  7. concentrationthen concentrated under reduced pressure
  8. customPurification of the residue by flash chromatography on silica gel (eluent: ethyl acetate/heptane 8:2)

Sources & evidence

ORD record
ord-a9bcb3ca33764b6bab816e47d789a44d
Source dataset
uspto-grants-2007_04
Patent number
US07199145B2

Reaction notes

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