Chloroethane → HCID 21070310, compound

HRID 1371544Notes

Reaction equation

HRID 1371544 reaction equation
[CH:1]([C:3]1[CH:42]=[CH:41][C:6]([CH2:7][CH:8]([NH:16][C:17](=[O:40])[CH2:18][CH:19]([NH:26][S:27]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)(=[O:29])=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9](=[O:15])[N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1)=O.Cl.[NH:44]1[CH2:47][CH2:46][CH2:45]1.C([BH3-])#N.[Na+].CC[Cl:54]>CO.CCOC(C)=O.CCOCC.CC(O)=O>[ClH:54].[N:44]1([CH2:1][C:3]2[CH:4]=[CH:5][C:6]([CH2:7][CH:8]([NH:16][C:17](=[O:40])[CH2:18][CH:19]([NH:26][S:27]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)(=[O:29])=[O:28])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9](=[O:15])[N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:41][CH:42]=2)[CH2:47][CH2:46][CH2:45]1

Participants

9

Reactant 4

HCID 6337ChloroethaneHCID 5003444Sodium cyanoborohydrideHCID 12308726Azetidine hydrochlorideHCID 21070329HCID 21070329, compound

Product 1

HCID 21070310HCID 21070310, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.489 g of the compound obtained in step A of Example 17 and 0.086 g of azetidine hydrochloride and 116 μl of TEA in 15 ml of MeOH is stirred for 1 hour at RT. Next, 0.072 ml of AcOH is added, the mixture is stirred for 15 minutes at RT, 0.079 g of sodium cyanoborohydride is added and the mixture is stirred for 2 hours at RT. The reaction mixture is concentrated under vacuum, the residue is extracted with DCM, the organic phase is washed with saturated NaHCO3 solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture (95/5; v/v) and then a DCM/MeOH/NH4OH mixture (95/5/0.5; v/v/v). The product obtained is dissolved in EtOAc, acidified to pH 1 by adding hydrochloric ether and diluted with ether, and the precipitate formed is filtered off by suction. 0.115 g of the expected product is obtained.

Workup

  1. stirringthe mixture is stirred for 15 minutes at RT
  2. stirringthe mixture is stirred for 2 hours at RT
  3. concentrationThe reaction mixture is concentrated under vacuum
  4. extractionthe residue is extracted with DCM
  5. washthe organic phase is washed with saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated off under vacuum
  8. customThe residue is chromatographed on silica gel
  9. washeluting with a DCM/MeOH mixture (95/5; v/v)
  10. customThe product obtained
  11. customthe precipitate formed
  12. filtrationis filtered off by suction

Sources & evidence

ORD record
ord-6b9b2ab5b8e84077a900a1beb7a3f372
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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