p-Toluenesulfonic acid → HCID 22730060, compound

HRID 2085676Notes

Reaction equation

HRID 2085676 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[C:40]12([CH2:50][NH:51][C:52]3[CH:57]=[CH:56][C:55]([S:58]([NH:61]C(=O)C4C=CC(I)=CC=4)(=[O:60])=[O:59])=[CH:54][C:53]=3[N+:71]([O-:73])=[O:72])[CH2:49][CH:44]3[CH2:45][CH:46]([CH2:48][CH:42]([CH2:43]3)[CH2:41]1)[CH2:47]2.CC1C=CC(S(O)(=O)=O)=CC=1>CC(O)(C)C.ClCCCl>[C:40]12([CH2:50][NH:51][C:52]3[CH:57]=[CH:56][C:55]([S:58]([NH:61][C:11](=[O:13])[C:10]4[CH:9]=[CH:8][C:7]([C:6]5[CH:5]=[CH:4][S:3][C:2]=5[Cl:1])=[CH:15][CH:14]=4)(=[O:60])=[O:59])=[CH:54][C:53]=3[N+:71]([O-:73])=[O:72])[CH2:49][CH:44]3[CH2:43][CH:42]([CH2:48][CH:46]([CH2:45]3)[CH2:47]1)[CH2:41]2

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 22730017HCID 22730017, compoundHCID 22730862HCID 22730862, compound

Product 1

HCID 22730060HCID 22730060, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6386tert-ButanolSolvent

Procedure

A room temperature mixture of Example 29A (39.4 mg, 0.17 mmol), resin-bound dicyclohexylcarbodiimide (225.0 mg, 1.83 mmol/g), and dimethylaminopyridine (60.0 mg, 4.95 mmol) was treated with a solution of Example 28A (40 mg, 0.11 mmol) in a 1:1 mixture of 1,2-dichloroethane and 2-methyl-2-propanol (3 mL), and agitated overnight on an Argonaut Technologies Quest 210. The mixture was treated with resin bound p-TsOH (990 mg, 1.44 mmol/g), agitated for 1 hour, decanted, and washed with dichloromethane. The combined extracts were concentrated and purified by HPLC using 0.1% TFA in H2O/CH3CN to provide the desired product. MS (APCI(+)) m/e 586 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ12.50 (s, 1H), 8.66 (d, 1H), 8.57 (t, 1H), 7.96 (d, 2H), 7.95 (dd, 1H), 7.71 (d, 2H), 7.59 (d, 1H), 7.36 (d, 1H), 7.29 (d, 1H), 7.29 (d, 1H), 3.17 (d, 2H), 1.97 (s, 3H), 1.58 (m, 12H).

Workup

  1. additionThe mixture was treated with resin
  2. stirringagitated for 1 hour
  3. customdecanted
  4. washwashed with dichloromethane
  5. concentrationThe combined extracts were concentrated
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-19068a53d2fb4458b84a1a530dc678bf
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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