Acetyl chloride → HCID 66756938, compound

HRID 1642608Notes

Reaction equation

HRID 1642608 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[S:15](=[O:17])(=[O:16])[N:14]([CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:13](=[O:24])[CH2:12]2)=[C:7]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=1.[C:37](Cl)(=[O:39])[CH3:38]>N1C=CC=CC=1.CCOC(C)=O>[CH2:26]([O:25][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[N:11]1[CH2:12][C:13](=[O:24])[N:14]([CH2:18][CH2:19][Si:20]([CH3:21])([CH3:22])[CH3:23])[S:15]1(=[O:16])=[O:17])[CH2:4][C:3]1[CH:33]=[CH:34][CH:35]=[CH:36][C:2]=1[NH:1][C:37](=[O:39])[CH3:38])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 66757115HCID 66757115, compound

Product 1

HCID 66756938HCID 66756938, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[4-(2-aminobenzyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (Example 4, Step A) (250 mg, 0.478 mmol) in pyridine (1.5 mL) is added acetylchloride (41 mg, 0.525 mmol). The mixture is stirred at ambient temperature for 30 min., then diluted with EtOAc and washed with 0.5N HCl, saturated NaHCO3 and brine. It is then dried over Na2SO4/MgSO4, filtered and concentrated to afford N-(2-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzyl}-phenyl)-acetamide as a gum: MS (M+H)+=566.1.

Workup

  1. washwashed with 0.5N HCl, saturated NaHCO3 and brine
  2. dry with materialIt is then dried over Na2SO4/MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cdd4d243af7f424c9336dacab5c01f56
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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