2-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acid → 2-(1-Hydroxy-4-(naphthalene-2-sulfonamido)naphthalen-2-ylthio)propanoic acid

HRID 1186682Notes

Reaction equation

HRID 1186682 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2S[CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][CH2:22][C:23]([OH:25])=[O:24].[C:26](O)(=S)C(C)O.Cl[C:33]1[C:42](=O)[C:41]2[C:36](=CC=CC=2)/[C:35](=N/S(C2C=CC3C(=CC=CC=3)C=2)(=O)=O)/[CH:34]=1>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[CH:20]=[CH:19][C:18]3[C:42](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:41]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][CH:22]([CH3:26])[C:23]([OH:25])=[O:24]

Participants

4

Reactant 3

HCID 15826052-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acidHCID 24282891(NE)-N-(3-chloro-4-oxonaphthalen-1-ylidene)naphthalene-2-sulfonamideHCID 178473673HCID 178473673, compound

Product 1

HCID 164824132-(1-Hydroxy-4-(naphthalene-2-sulfonamido)naphthalen-2-ylthio)propanoic acid

Procedure

5.2.64 2-(1-hydroxy-4-(naphthalene-2-sulfonamido)naphthalen-2-ylthio)propanoic acid (14v) was prepared according to the procedure of procedure B for 10a except using thiolactic acid and (E)-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)naphthalene-2-sulfonamide (12f), which afforded the title compound 51.3 mg (58.6%) as an off-white solid, m.p.: 176-178° C.

Sources & evidence

ORD record
ord-23c2275f2c694d5fa2a383cdc3e30a0c
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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