m-Chloroperbenzoic acid → HCID 141551043, compound

HRID 1252314Notes

Reaction equation

HRID 1252314 reaction equation
[CH:1]([O:14][C:15]([C:17]1([O:22]/[N:23]=[C:24](/[C:55]2[N:56]=[C:57]([NH:60][C:61]([C:74]3[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=3)([C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=3)[C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[S:58][CH:59]=2)\[C:25]([NH:27][CH:28]2[C:53](=[O:54])[N:30]3[C:31]([C:37]([O:39][CH:40]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:38])=[C:32]([CH2:35][Cl:36])[CH2:33][S:34][C@H:29]23)=[O:26])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:88])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]([O:14][C:15]([C:17]1([O:22]/[N:23]=[C:24](/[C:55]2[N:56]=[C:57]([NH:60][C:61]([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)([C:68]3[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=3)[C:74]3[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=3)[S:58][CH:59]=2)\[C:25]([NH:27][CH:28]2[C:53](=[O:54])[N:30]3[C:31]([C:37]([O:39][CH:40]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)=[O:38])=[C:32]([CH2:35][Cl:36])[CH2:33][S:34](=[O:88])[C@H:29]23)=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21]1)=[O:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178525023HCID 178525023, compound

Product 1

HCID 141551043HCID 141551043, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The residue obtained in (A) was dissolved in 50 ml of methylene chloride, and 710 mg (3.3 mmol) of m-chloroperbenzoic acid (purity: 80%) was added under cooling with ice. The mixture was stirred for 20 minutes. Then, 30 ml of methylene chloride and 40 ml of a 5% sodium bicarbonate aqueous solution were added to the reaction solution. The organic layer was separated and washed with water and with a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and then concentrated to obtain the residue of the above identified compound, which was used for the subsequent reaction without purification.

Workup

  1. temperatureunder cooling with ice
  2. customThe organic layer was separated
  3. washwashed with water and with a saturated sodium chloride aqueous solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain the residue of the
  7. customwas used for the subsequent reaction without purification

Sources & evidence

ORD record
ord-dbc1a2cc613f4c2f8b6fe3a1fa2d3f49
Source dataset
uspto-grants-1988_05
Patent number
US04742053

Reaction notes

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