Phenyl isocyanate → (5RS, 6SR)-6-methyl-2,6-diphenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine

HRID 982262Notes

Reaction equation

HRID 982262 reaction equation
[C:1]1([C:7]2[O:8][C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([CH3:14])[CH:10]([OH:13])[CH2:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH3:14][C:9]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[O:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:12][CH2:11][CH:10]1[O:13][C:28](=[O:29])[NH:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 14650626(5RS, 6SR)-2,6-diphenyl-6-methyl-5,6-dihydro-4H-1,3-oxazin-5-ol

Product 1

HCID 14650663(5RS, 6SR)-6-methyl-2,6-diphenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazineYield 82.1%

Procedure

Working in a manner similar to that described in Example 12, but starting with (5RS, 6SR)-2,6-diphenyl-6-methyl-5,6-dihydro-4H-1,3-oxazin-5-ol (0.8 g) and phenyl isocyanate (1.8 g), and after purification of the solid obtained by chromatography on a column (height: 30 cm; diameter: 2.5 cm) of silica (0.2-0.063 mm), eluting with a mixture of cyclohexane and ethyl acetate (80:20 by volume) and collecting 20cc fractions, fractions 1 to 5 being combined and concentrated to dryness under reduced pressure (4 kPa) at 45° C., followed by recrystallization of the residue in acetonitrile (12 cc), (5RS, 6SR)-6-methyl-2,6-diphenyl-5-phenylcarbamoyloxy-5,6-dihydro-4H-1,3-oxazine (0.95 g), m.p. 180° C., is obtained.

Workup

  1. customafter purification of the solid
  2. customobtained by chromatography on a column (height: 30 cm; diameter: 2.5 cm) of silica (0.2-0.063 mm)
  3. washeluting with a mixture of cyclohexane and ethyl acetate (80:20 by volume)
  4. customcollecting 20cc fractions, fractions 1 to 5 being
  5. concentrationconcentrated to dryness under reduced pressure (4 kPa) at 45° C.
  6. customfollowed by recrystallization of the residue in acetonitrile (12 cc)

Sources & evidence

ORD record
ord-426869f1b8fc46a4b8df20f4a70596af
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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