6-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid → 3-Benzyloxy-4-oxo-6-[(toluene-4-sulfonylamino)-methyl]-4H-pyran-2-carboxylic acid

HRID 1846877Notes

Reaction equation

HRID 1846877 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:29])[CH:11]=[C:12]([CH2:17][NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[O:13][C:14]=1[CH:15]=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(S(C(N)C2OC(C(O)=O)=C(OCC3C=CC=CC=3)C(=O)C=2)(=O)=[O:37])C=CC=CC=1>>[CH2:1]([O:8][C:9]1[C:10](=[O:29])[CH:11]=[C:12]([CH2:17][NH:18][S:19]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)(=[O:21])=[O:20])[O:13][C:14]=1[C:15]([OH:37])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 867256956-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acidHCID 86725733N-(5-Benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-4-methyl-benzenesulfonamide

Product 1

HCID 867257343-Benzyloxy-4-oxo-6-[(toluene-4-sulfonylamino)-methyl]-4H-pyran-2-carboxylic acidYield 80.14%

Procedure

3-Benzyloxy-4-oxo-6-[(toluene-4-sulfonylamino)-methyl]-4H-pyran-2-carboxylic acid (12-06) (2.0 g, 80.14%) was synthesized as a white solid from N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-4-methyl-benzenesulfonamide (11-06) (2.4 g, 5.81 mmol) following the procedure described for 6-(benzenesulfonylamino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (12-01).

Sources & evidence

ORD record
ord-2b5569876b314ac5a8cf1408754486a1
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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