4-(Chlorosulfonyl)benzoic acid → HCID 86679575, compound

HRID 1776616Notes

Reaction equation

HRID 1776616 reaction equation
[NH2:1][CH2:2][C:3]([O:5][C@H:6]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH:24]([F:26])[F:25])=[C:19]([O:27][CH2:28][CH:29]2[CH2:31][CH2:30]2)[CH:18]=1)[CH2:7][C:8]1[C:13]([Cl:14])=[CH:12][N+:11]([O-:15])=[CH:10][C:9]=1[Cl:16])=[O:4].Cl[S:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40]([OH:42])=[O:41])=[CH:38][CH:37]=1)(=[O:35])=[O:34]>Cl>[C:40]([C:39]1[CH:38]=[CH:37][C:36]([S:33]([NH:1][CH2:2][C:3]([O:5][C@H:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([F:26])[F:25])=[C:19]([O:27][CH2:28][CH:29]3[CH2:31][CH2:30]3)[CH:18]=2)[CH2:7][C:8]2[C:13]([Cl:14])=[CH:12][N+:11]([O-:15])=[CH:10][C:9]=2[Cl:16])=[O:4])(=[O:35])=[O:34])=[CH:44][CH:43]=1)([OH:42])=[O:41]

Participants

4

Reactant 2

HCID 823854-(Chlorosulfonyl)benzoic acidHCID 86679414HCID 86679414, compound

Product 1

HCID 86679575HCID 86679575, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(S)-4-(2-(2-aminoacetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)ethyl)-3,5-dichloropyridine 1-oxide (prepared in an analogous manner as described in Scheme 1, Step 1-2) (100 mg, 0.210 mmol) was dissolved in py (2.5 ml). 4-(chlorosulfonyl)benzoic acid (60.1 mg, 0.272 mmol) was added, and the reaction was stirred at RT for 4 hours. The reaction mixture was diluted with HCl 1N and extracted with EtOAc. The organic phase was washed with HCl 1N and brine, dried over Na2SO4 and concentrated under vacuum to give (S)-4-(2-(2-(4-carboxyphenylsulfonamido)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (120 mg, 87% yield).

Workup

  1. dissolutionwas dissolved in py (2.5 ml)
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with HCl 1N and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ab027128119f48249e78b751fee1d8a6
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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