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

HRID 1846869Notes

Reaction equation

HRID 1846869 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][CH:25]=[C:24]([Cl:28])[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:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)(=[O:21])=[O:20])[O:13][C:14]=1[C:15]([OH:37])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 867256956-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acidHCID 86725726N-(5-Benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-3-chloro-benzenesulfonamide

Product 1

HCID 867257273-Benzyloxy-6-[(3-chloro-benzenesulfonylamino)-methyl]-4-oxo-4H-pyran-2-carboxylic acidYield 89.25%

Procedure

3-Benzyloxy-6-[(3-chloro-benzenesulfonylamino)-methyl]-4-oxo-4H-pyran-2-carboxylic acid (12-05) (2.04 g, 89.25%) was synthesized as a white solid from N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-3-chloro-benzenesulfonamide (11-05) (2.2 g, 5.08 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-c3d715c6fec34481aee688abf0620a24
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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