3-Aminosalicylic acid → 2-(4-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenyl)benzo[d]oxazole-7-carboxylic acid

HRID 415138Notes

Reaction equation

HRID 415138 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:11].Cl[C:13]([C:15]1[CH:33]=[CH:32][C:18]([CH2:19][N:20]([CH3:31])[C:21](=[O:30])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:17][CH:16]=1)=O>>[CH2:23]([O:22][C:21]([N:20]([CH2:19][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[O:11][C:3]3[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=[CH:10][C:2]=3[N:1]=2)=[CH:33][CH:32]=1)[CH3:31])=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 684433-Aminosalicylic acidHCID 86633082Benzyl 4-(chlorocarbonyl)benzyl(methyl)carbamate

Product 1

HCID 666212862-(4-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenyl)benzo[d]oxazole-7-carboxylic acid

Procedure

2-(4-(((Benzyloxycarbonyl)(methyl)amino)methyl)phenyl)benzo[d]oxazole-7-carboxylic acid is prepared from 3-aminosalicylic acid and benzyl 4-(chlorocarbonyl)benzyl(methyl)carbamate using identical conditions described in Example 3A. MS (ESI) m/e 417 [M+H]+.

Sources & evidence

ORD record
ord-cf36b0e70f99439289a1fac7c2512d44
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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