Water → HCID 9864334, compound

HRID 609552Notes

Reaction equation

HRID 609552 reaction equation
[Br-].[Al+3].[Br-].[Br-].C(S)C.[CH2:8]([C:12]1([CH2:33][CH3:34])[CH2:18][N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[CH:26][C:27]([O:29]C)=[CH:28][C:15]=2[S:14](=[O:32])(=[O:31])[CH2:13]1)[CH2:9][CH2:10][CH3:11].O>C(Cl)Cl>[CH2:8]([C:12]1([CH2:33][CH3:34])[CH2:18][N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:15]=2[S:14](=[O:31])(=[O:32])[CH2:13]1)[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 166749BromhydrolHCID 19599355HCID 19599355, compound

Product 1

HCID 9864334HCID 9864334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of aluminum bromide (1M in CH2Cl2, 16 mmol) and ethanethiol (7.4 ml, 100 mmol) at 0° C. was added the compound of Example 17 (0.78 g, 2.01 mmol) in 30 ml CH2Cl2. The mixture was stirred for 1 h at 0° C. and then 25 ml water was added and the product extracted with 3×20 ml CH2Cl2. The organic layer was dried and the solvents evaporated. The residue was applied to a silica gel column and the product eluted with 35% ethyl acetate/petroleum ether (0.74 g, 98%). 1H NMR (DMSO-d6) δ 10.00 (s, 1H), 7.28-6.74 (m, 8H); 3.6 (br s, 2H); 3.21 (s, 2H); 1.55-1.02 (m, 8H); 0.73 (m, 6H). MS Da/e=374 (MH+). Calcd for C21H27NSO3 ×0.4 H2O: C, 66.25; H, 7.36; N, 3.68; S, 8.42. Found: C, 66.12; H. 7.37; N, 3.61; S, 8.30.

Workup

  1. extractionthe product extracted with 3×20 ml CH2Cl2
  2. customThe organic layer was dried
  3. customthe solvents evaporated
  4. washthe product eluted with 35% ethyl acetate/petroleum ether (0.74 g, 98%)

Sources & evidence

ORD record
ord-86018cc0496048e691b6cba855e61c6d
Source dataset
uspto-grants-1999_12
Patent number
US05998400

Reaction notes

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