Tris(hydroxymethyl)aminomethane → (RS)-5-[3,5-dihydroxy-4-(2-oxo-2-phenylethoxy)-benzoyl]-3,3-bis(hydroxymethyl)-8a-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-8(8aH)-one

HRID 2393058Notes

Reaction equation

HRID 2393058 reaction equation
O[C:2]1[C:7]([OH:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[C:16]([OH:18])[C:15]([O:19][CH2:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([OH:29])[CH:13]=1)=[O:11].[CH2:30]([OH:37])[C:31]([NH2:36])([CH2:34][OH:35])[CH2:32][OH:33]>[Ag]=O>[OH:29][C:14]1[CH:13]=[C:12]([CH:17]=[C:16]([OH:18])[C:15]=1[O:19][CH2:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10]([C:3]1[CH:4]=[CH:5][C:6](=[O:9])[C:7]2([OH:8])[O:37][CH2:30][C:31]([CH2:34][OH:35])([CH2:32][OH:33])[NH:36][C:2]=12)=[O:11]

Participants

4

Reactant 2

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 15184924[2,3,4-Trihydroxy-phenyl][3',5'-dihydroxy-4'-(2-oxo-2-phenylethoxy)phenyl] methanone

Product 1

HCID 10097374(RS)-5-[3,5-dihydroxy-4-(2-oxo-2-phenylethoxy)-benzoyl]-3,3-bis(hydroxymethyl)-8a-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-8(8aH)-oneYield 40.3%

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

The procedure is analogous to that described in Example 8a), but starting with 0.79 g of [2,3,4-trihydroxy-phenyl][3',5'-dihydroxy-4'-(2-oxo-2-phenylethoxy)phenyl] methanone (compound VIIIb described in Example 2), 12.10 g of Tris and 2.30 g of silver oxide (Ag2O). After purification by chromatography on a 30 g silica gel column (diameter: 2.0 cm, height: 60 cm) eluted with an ethyl acetate/methanol mixture (97/3 by volume), 0.40 g of (RS)-5-[3,5-dihydroxy-4-(2-oxo-2-phenylethoxy)-benzoyl]-3,3-bis(hydroxymethyl)-8a-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-8(8aH)-one is obtained in the form of an orange powder melting at around 185° C. (with decomposition).

Workup

  1. customAfter purification by chromatography on a 30 g silica gel column (diameter: 2.0 cm, height: 60 cm)
  2. washeluted with an ethyl acetate/methanol mixture (97/3 by volume)

Sources & evidence

ORD record
ord-efe83cc74144424db134ef5bc74f95c8
Source dataset
uspto-grants-1998_09
Patent number
US05804580

Reaction notes

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