Hydrochloric Acid → HCID 86622309, compound

HRID 501668Notes

Reaction equation

HRID 501668 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:3].CCN(C(C)C)C(C)C.Cl.[NH2:19][C@@H:20]([CH2:25][CH:26]=[CH2:27])[C:21]([O:23][CH3:24])=[O:22].Cl>C(Cl)Cl>[CH2:5]([O:4][C:2]([NH:19][C@@H:20]([CH2:25][CH:26]=[CH2:27])[C:21]([O:23][CH3:24])=[O:22])=[O:3])[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 61140Butyl chloroformateHCID 81531DiisopropylethylamineHCID 86622306HCID 86622306, compound

Product 1

HCID 86622309HCID 86622309, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step E (1): Butyl chloroformate (408 mg, 3.0 mmol), followed by DIEA (1.23 mL, 9.0 mmol), was added to a 250-mL single neck round bottom flask charged with a solution of the (S)-methyl 2-aminopent-4-enoate hydrochloride (500 mg, 3.00 mmol) in DCM (50 mL) at 0° C. Warmed the mixture to rt and after 2 h, poured into 1N HCl (200 mL). Extracted with EtOAc. Washed the combined organic extracts with 0.1 N NaOH, brine, dried over MgSO4, filtered and concentrated in vacuo. Purification by silica-gel column chromatography afforded 357 mg (52% yield) of (S)-methyl 2-(butoxycarbonylamino)pent-4-enoate. LC-MS (M+H)+=230.2; 1H NMR (500 MHz, CDCl3) δ ppm 0.91 (t, J=7.48 Hz, 3H) 1.30-1.40 (m, 2H) 1.54-1.61 (m, 2H) 2.43-2.59 (m, 2H) 3.73 (s, 3H) 4.05 (t, J=6.71 Hz, 2H) 4.38-4.46 (m, 1H) 5.08-5.20 (m, 3H) 5.62-5.72 (m, 1H).

Workup

  1. additionwas added to a 250-mL single neck round bottom flask
  2. extractionExtracted with EtOAc
  3. washWashed the combined organic extracts with 0.1 N NaOH, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica-gel column chromatography

Sources & evidence

ORD record
ord-7914764e57724063998a4214c6610aa0
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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