4-(2,3-Epoxypropoxy)salicylic acid methyl ester → 1-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethyl]benzylamino]-3-(3-hydroxy-4-methoxycarbonylphenoxy)propan-2-ol

HRID 4545

Reaction equation

HRID 4545 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:5](=[CH:7][C:8]([O:11][CH2:12][CH:13]2[O:15][CH2:14]2)=[CH:9][CH:10]=1)[OH:6].[CH2:17]([NH:24][CH:25]([CH3:38])[CH2:26][O:27][C:28]1[CH:36]=[C:32]([C:33]([NH2:35])=[O:34])[C:31]([OH:37])=[CH:30][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)(C)C>[C:33]([C:32]1[CH:36]=[C:28]([CH:29]=[CH:30][C:31]=1[OH:37])[O:27][CH2:26][CH:25]([N:24]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:14][CH:13]([OH:15])[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:4]([C:3]([O:2][CH3:1])=[O:16])=[C:5]([OH:6])[CH:7]=1)[CH3:38])(=[O:34])[NH2:35]

Participants

4

Reactant 2

HCID 126113354-(2,3-Epoxypropoxy)salicylic acid methyl esterHCID 137543345-(2-Benzylaminopropoxy)salicylamide

Product 1

HCID 536956571-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethyl]benzylamino]-3-(3-hydroxy-4-methoxycarbonylphenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

After 40 hours' boiling and working up analogously to Example (4a), 22.4 g of 4-(2,3-epoxypropoxy)salicylic acid methyl ester and 30 g of 5-(2-benzylaminopropoxy)salicylamide in 200 ml of isopropanol yield crude 1-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethyl]benzylamino]-3-(3-hydroxy-4-methoxycarbonylphenoxy)propan-2-ol as a light-coloured foam which is further processed as a crude product.

Sources & evidence

ORD record
ord-7f10f021005f4af18df8b64a1ea0e211
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Linked notes

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