Dicyclohexylcarbodiimide → HCID 53987405, compound

HRID 400135Notes

Reaction equation

HRID 400135 reaction equation
[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1.[Si:35]([O:42][C@H:43]1[CH2:52][C@H:51](O)[C@H:50]2[C:45]([CH:46]=[CH:47][C@H:48]([CH3:71])[C@@H:49]2[CH2:54][CH2:55][C@H:56]2[O:61][C:60](=[O:62])[CH2:59][C@H:58]([O:63][Si:64]([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:66])[CH3:65])[CH2:57]2)=[CH:44]1)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]>C(Cl)Cl>[Si:35]([O:42][C@H:43]1[CH2:52][C@H:51]([O:5][C:4](=[O:6])[CH2:3][C:2]([CH3:8])([CH3:7])[CH3:1])[C@H:50]2[C:45]([CH:46]=[CH:47][C@H:48]([CH3:71])[C@@H:49]2[CH2:54][CH2:55][C@H:56]2[O:61][C:60](=[O:62])[CH2:59][C@H:58]([O:63][Si:64]([C:67]([CH3:70])([CH3:69])[CH3:68])([CH3:65])[CH3:66])[CH2:57]2)=[CH:44]1)([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 14057tert-Butylacetic acidHCID 755674-PyrrolidinopyridineHCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether

Product 1

HCID 53987405HCID 53987405, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.46 ml (3.6 mmol) of 3,3-dimethylbutyric acid, 741 mg (3.6 mmol) of dicyclohexyl carbodiimide and 13 mg (0.09 mmol) of 4-(1-pyrrolidinyl)pyridine were added to a solution of 1.00 g (1.8 mmol) of (4R,6R)-6-{2-[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example B, above] in 15 ml of methylene chloride, whilst ice-cooling. The resulting mixture was stirred at the same temperature for 30 minutes and then stirred at room temperature for a further 19 hours. At the end of this time, the solvent was removed by distillation under reduced pressure and the resulting residue was mixed with 20 ml of diethyl ether. Any insoluble material was removed by filtration and then washed twice with diethyl ether, using 5 ml for each washing. The filtrate and the washings were then combined and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 555 mg (47% yield) of the title compound.

Workup

  1. customprepared
  2. stirringstirred at room temperature for a further 19 hours
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. additionthe resulting residue was mixed with 20 ml of diethyl ether
  5. customAny insoluble material was removed by filtration
  6. washwashed twice with diethyl ether
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe resulting residue was purified by flash column chromatography through silica gel
  9. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-898fbef8cfc7426686b02ad7530fd3a1
Source dataset
uspto-grants-1998_10
Patent number
US05827855

Reaction notes

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