Toluene → HCID 12990928, compound

HRID 1827996Notes

Reaction equation

HRID 1827996 reaction equation
[N-:1]=[C:2]=[O:3].[CH3:4][O:5][C:6](=[O:16])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:8].[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C>[CH3:4][O:5][C:6](=[O:16])[C@H:7]([NH:8][C:6]([O:16][CH2:23][C:17]1[CH:22]=[CH:21][C:20]2[O:3][C:2]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:1][C:19]=2[CH:18]=1)=[O:5])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 86584107HCID 86584107, compound

Product 1

HCID 12990928HCID 12990928, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of 2-(phenylbenzoxazol-5-yl)methanol 58 (215 mg, 0.95 mmol), (R)-2-isocyanato-3-phenylpropionic acid methyl ester 5(196 mg, 0.95 mmol), DMAP (12 mg, 0.095 mmol) and toluene (12 ml) was heated at reflux under an atmosphere of N2 for 3 hrs. The solvent was removed under reduced pressure and the residue purified by chromatography to yield 381 mg of (R)-2-(2-Phenylbenzoxazol-5-ylmethoxycarbonylamino)-3-phenylpropionic acid methyl ester 59.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of N2 for 3 hrs
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-e6d2dc3d236d4e6fa74352f5ac3f8d9a
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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