((p-(Benzyloxy)phenoxy)methyl)oxirane → 1-[N-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethyl]benzylamino]-3-(4-benzyloxyphenoxy)propan-2-ol

HRID 4529

Reaction equation

HRID 4529 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]2[O:19][CH2:18]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([NH:27][CH:28]([CH3:44])[CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]2[O:39][C:38]([CH3:41])([CH3:40])[NH:37][C:36](=[O:42])[C:35]=2[CH:43]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(C)C>[CH3:41][C:38]1([CH3:40])[NH:37][C:36](=[O:42])[C:35]2[CH:43]=[C:31]([O:30][CH2:29][CH:28]([N:27]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18][CH:17]([OH:19])[CH2:16][O:15][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:14][CH:13]=3)[CH3:44])[CH:32]=[CH:33][C:34]=2[O:39]1

Participants

4

Reactant 2

HCID 119882((p-(Benzyloxy)phenoxy)methyl)oxiraneHCID 137544146-(2-benzylaminopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one

Product 1

HCID 137544111-[N-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethyl]benzylamino]-3-(4-benzyloxyphenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 15.4 g of benzyl [4-(2,3-epoxypropoxy)phenyl]ether and 17.0 g of 6-(2-benzylaminopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one in 100 ml of isopropanol is refluxed for 24 hours, filtered and concentrated by evaporation. Trituration of the residue with approximately 200 ml of ether results in crystallisation of 1-[N-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethyl]benzylamino]-3-(4-benzyloxyphenoxy)propan-2-ol having a melting point of 149°-160° (in which the enantiomer pair A is present in greater amount).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-75fb8b38e64d40b591e7fff45e062a05
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Linked notes

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