Benzoic acid, 3-(chlorosulfonyl)- → HCID 60054801, compound

HRID 489242Notes

Reaction equation

HRID 489242 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@:12]3([C@H:18]([C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)[CH2:17][NH:16][CH2:15]3)[N:11]([CH2:27][CH3:28])[C:10]2=[O:29])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[S:31]([C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37]([OH:39])=[O:38])(=[O:33])=[O:32].CCN(C(C)C)C(C)C>C1COCC1>[C:23]([C:22]1[CH:21]=[CH:20][C:19]([C@H:18]2[C@:12]3([N:11]([CH2:27][CH3:28])[C:10](=[O:29])[N:9]([C:4]4[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=4)[C:13]3=[O:14])[CH2:15][N:16]([S:31]([C:34]3[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=3)[C:37]([OH:39])=[O:38])(=[O:33])=[O:32])[CH2:17]2)=[CH:26][CH:25]=1)#[N:24]

Participants

5

Reactant 3

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 81531DiisopropylethylamineHCID 60054638HCID 60054638, compound

Product 1

HCID 60054801HCID 60054801, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of Example 50 (100 mg, 0.23 mmol) and 3-(chlorosulfonyl)benzoic acid (57 mg, 0.26 mmol) in THF (5 ml) was added DIEA (45 μl, 0.26 mmol) at room temperature. The reaction mixture was stirred at room temperature for 24 hours then concentrated under vacuum. The residue was partitioned between EtOAc and water. The pH was adjusted to pH=2. The aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The obtained solid was chromatofraphed over silica gel using DCM/MeOH (80/20) to yield the above-titled compound (63 mg), mp=145° C. 1H NMR (CDCl3): 8.63 (1H, s), 8.41 (1H, d, J=7.5 Hz), 8.17 (1H, d, J=7.4 Hz), 7.77 (1 H, t, J=7.7 Hz), 7.62 (2H, d, J=7.7 Hz), 7.18-7.26 (3H, m), 6.60 (2H, s), 3.4-4.2 (7H, m), 1.45 (3H, t, J=6.8 Hz).

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4b2f59319a2c4c92af9546c90aaac107
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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