1,2-Dichloroethane → HCID 86758351, compound

HRID 2229221Notes

Reaction equation

HRID 2229221 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[C:10](=[O:21])[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([NH2:19])=[C:14]([Cl:20])[CH:13]=2)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].CO[CH:24]1[CH2:28][CH2:27][CH:26](OC)O1.C(O)(=O)C.ClCCCl>O.C(Cl)Cl.CO>[CH2:1]([O:3][P:4]([C:9]1[C:10](=[O:21])[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([N:19]1[CH:24]=[CH:28][CH:27]=[CH:26]1)=[C:14]([Cl:20])[CH:13]=2)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 790982,5-Dimethoxytetrahydrofuran2×HCID 15511753HCID 15511753, compound

Product 1

HCID 86758351HCID 86758351, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
75 °C

Procedure

A biphasic suspension of 2.43 g (7.35 mmol) of the compound obtained in Step D of Example 1 and 1.33 ml (10.29 mmol) of 2,5-dimethoxytetrahydrofuran in a mixture of 24 ml of distilled water, 12 ml of acetic acid and 36 ml of 1,2-dichloroethane is stirred vigorously at 75° C. for 60 minutes. In TLC (CH2Cl2/MeOH 9:1), a small amount of starting material is still observed. 0.2 eq. of 2,5-dimethoxytetrahydrofuran (2.06 mmol, 0.26 ml) is added, and heating is maintained for 30 minutes. The mixture is left to return to room temperature and extraction is carried out with CH2Cl2. The organic phase is washed 4 times with water and then with a saturated NaCl solution. Drying is carried out over MgSO4, followed by evaporation and chromatography of the resulting oil over 200 g of Merck 7734 silica whilst eluting with a mixture of CH2Cl2/MeOH 95:5. An oil corresponding to the title product is obtained, which is crystallised from isopropyl ether.

Workup

  1. temperatureheating
  2. temperatureis maintained for 30 minutes
  3. waitThe mixture is left
  4. customto return to room temperature
  5. extractionextraction
  6. washThe organic phase is washed 4 times with water
  7. customDrying
  8. customfollowed by evaporation and chromatography of the resulting oil over 200 g of Merck 7734 silica
  9. washwhilst eluting with a mixture of CH2Cl2/MeOH 95:5

Sources & evidence

ORD record
ord-110df0efd9fd49ad8c8f6841ba6f8c03
Source dataset
uspto-grants-2002_07
Patent number
US06420386B1

Reaction notes

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