Ethyl chloroformate → HCID 71073409, compound

HRID 2408940Notes

Reaction equation

HRID 2408940 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:50])[C:25]([C:27]4([NH:31][C:32](=[O:49])[CH:33]([NH:41][C:42]([O:44][C:45](C)(C)[CH3:46])=[O:43])[CH2:34][C:35]5([F:40])[CH2:39][CH2:38][CH2:37][CH2:36]5)[CH2:30][CH2:29][CH2:28]4)=[O:26])=[N:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.ClC(OCC)=O>Cl.O1CCOCC1>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:50])[CH:25]([C:27]4([NH:31][C:32](=[O:49])[CH:33]([NH:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:34][C:35]5([F:40])[CH2:39][CH2:38][CH2:37][CH2:36]5)[CH2:28][CH2:29][CH2:30]4)[OH:26])=[N:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 71073351HCID 71073351, compound

Product 1

HCID 71073409HCID 71073409, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 57-e (0.079 mmol) was dissolved in 4M HCl in dioxane (3 mL) and then stirred for 4 hrs at room temperature. The solution was concentrated under vacuum and the crude portioned between aq. K2CO3 (0.5 M) and DCM. The aqueous phase was extracted with EtOAc, the combined organic layers were dried over anh. Na2SO4 and concentrated under vacuum. The resulting amine was dissolved in dry DCM (3 mL) and an excess of solid NaHCO3 was added, followed by addition of ethyl chloroformate (7.5 μL, 0.079 mmol). The reaction was stirred for 2 hrs, then filtered and concentrated. (MS m/z 662.05 (M+H).+ The crude compound was used in next step without further purification.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over anh. Na2SO4
  4. concentrationconcentrated under vacuum
  5. dissolutionThe resulting amine was dissolved in dry DCM (3 mL)
  6. additionan excess of solid NaHCO3 was added
  7. stirringThe reaction was stirred for 2 hrs
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custom(MS m/z 662.05 (M+H).+ The crude compound was used in next step without further purification

Sources & evidence

ORD record
ord-e5d60938997d4200a6f61a0ef1b43dff
Source dataset
uspto-grants-2014_08
Patent number
US08815809B2

Reaction notes

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