Pyridine → HCID 53952393, compound

HRID 1729539Notes

Reaction equation

HRID 1729539 reaction equation
CC1C2C34C(=CC(=O)C=2NC=1)[N:11]([C:16]([C:18]1[NH:26][C:25]2[C:20](=[C:21]5[CH2:32][CH2:31][N:30]([C:33]([C:35]6[NH:43][C:42]7[C:37](=[C:38]8[CH2:49][CH2:48][N:47]([C:50]([NH2:52])=[O:51])[C:39]8=[C:40]([OH:46])[C:41]=7[O:44][CH3:45])[CH:36]=6)=[O:34])[C:22]5=[C:23]([OH:29])[C:24]=2[O:27][CH3:28])[CH:19]=1)=[O:17])[CH2:10]C3C4.[C:53]([Cl:60])(=O)[CH2:54][CH2:55][CH2:56][CH2:57][CH3:58].ClC1C=CC=CC=1O.[C:69]([O-:76])(=[O:75])[CH2:70][CH2:71][CH2:72][CH2:73][CH3:74].[N:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1>>[C:69]([O:76][C:58]1[C:82]2[NH:77][CH:78]=[C:80]([CH3:79])[C:81]=2[C:55]2[C@H:54]([CH2:53][Cl:60])[CH2:10][N:11]([C:16]([C:18]3[NH:26][C:25]4[C:24]([O:27][CH3:28])=[C:23]([OH:29])[C:22]5[N:30]([C:33]([C:35]6[NH:43][C:42]7[C:41]([O:44][CH3:45])=[C:40]([OH:46])[C:39]8[N:47]([C:50]([NH2:52])=[O:51])[CH2:48][CH2:49][C:38]=8[C:37]=7[CH:36]=6)=[O:34])[CH2:31][CH2:32][C:21]=5[C:20]=4[CH:19]=3)=[O:17])[C:56]=2[CH:57]=1)(=[O:75])[CH2:70][CH2:71][CH2:72][CH2:73][CH3:74]

Participants

6

Reactant 5

HCID 1049PyridineHCID 72452-Chlorophenol2×HCID 67340Hexanoyl chloride2×HCID 73240CC-1065HCID 4398339Hexanoate2×

Product 1

HCID 53952393HCID 53952393, compound

Procedure

An 11 mg (0.016 mmole) quantity CC-1065 is dissolved in 150 μl pyridine. Add 4 μl hexanoyl chloride and follow the reaction by HPLC. Two more 4 μl portions of hexanoyl chloride are added after 35 and 70 minutes reaction time. (The reaction to the intermediate chlorophenol is fast but acylation to the desired hexanoate is not only slow but also not entirely selective since an even less polar product appears before all the chlorophenol has been converted to the desired hexanoate.) After a total of 3 hours reaction, the mixture is transferred to a conical test tube, and washed with 100 μl pyridine. Then 5 ml water is added and a solid precipitates. The solid is spun down in a centrifuge and the liquid phase removed. This procedure is repeated with 5 ml water and 1.5 ml methanol. The solid is then dried under vacuum. HPLC of the 3 washes shows only small amounts of material present as a mixture of product and less polar side product.

Workup

  1. customthe reaction by HPLC
  2. customafter 35 and 70 minutes reaction time
  3. custom) After a total of 3 hours reaction
  4. customthe mixture is transferred to a conical test tube
  5. washwashed with 100 μl pyridine
  6. additionThen 5 ml water is added
  7. customa solid precipitates
  8. customthe liquid phase removed
  9. customThe solid is then dried under vacuum
  10. additionpresent as a mixture of product and less polar side product

Sources & evidence

ORD record
ord-1b458b35d7684d8d8ffcc153632aa08d
Source dataset
uspto-grants-1994_07
Patent number
US05332837

Reaction notes

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