Benzoyl chloride → HCID 17751500, compound

HRID 643929Notes

Reaction equation

HRID 643929 reaction equation
[K].[OH:2][C:3]1[C:4]([N:15]2[S:19](=[O:21])(=[O:20])[NH:18][C:17](=[O:22])[CH2:16]2)=[CH:5][C:6]2[CH2:7][C:8]([CH3:14])([CH3:13])[CH2:9][CH2:10][C:11]=2[CH:12]=1.OC1C(N2S(=O)(=O)NC(=O)C2)=CC2CC(C)(C)CCC=2C=1.CC(C)([O-])C.[K+].[C:50](Cl)(=[O:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C=O)C>[CH3:13][C:8]1([CH3:14])[CH2:9][CH2:10][C:11]2[CH:12]=[C:3]([O:2][C:50](=[O:57])[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:4]([N:15]3[CH2:16][C:17](=[O:22])[NH:18][S:19]3(=[O:21])=[O:20])=[CH:5][C:6]=2[CH2:7]1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 17751466HCID 17751466, compoundHCID 23665647Potassium tert-butoxideHCID 66751087HCID 66751087, compound

Product 1

HCID 17751500HCID 17751500, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(3-hydroxy-7,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt (47 mg, 0.14 mmol; prepared from the title compound of Example 49 analogously to procedure as described in Example 1, step I) in DMF (3 mL) at 0° C. is added potassium t-butoxide (1M in THF, 0.13 mL,). After 5 min, benzoyl chloride (0.016 mL, 0.14 mmol) is added. The mixture is stirred at 0° C. for 5 min. The mixture is partitioned between Et2O and aq. K2CO3. The ether layer is removed. The aqueous layer is acidified by adding 3M HCl solution, and Et2O is added to extract the product. The organic residue is purified by HPLC to give the title compound as a solid: 1H NMR (CD3OD) δ 1.02 (s, 6H), 1.62 (t, J=7 Hz, 2H), 2.59 (s, 2H), 2.88 (t, J=7 Hz, 2H), 4.43 (s, 2H), 7.11 (s, 1H), 7.23 (s, 1H), 7.52-7.55 (m, 2H), 7.65-7.69 (m, 1H), 8.16-8.19 (m, 2H); (M+H)+=413.

Workup

  1. customat 0° C.
  2. customThe mixture is partitioned between Et2O and aq. K2CO3
  3. customThe ether layer is removed
  4. additionby adding 3M HCl solution, and Et2O
  5. additionis added
  6. extractionto extract the product
  7. customThe organic residue is purified by HPLC

Sources & evidence

ORD record
ord-4f50245d4fa048dbacd26c527464d940
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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