Hydrochloric Acid → HCID 89668253, compound

HRID 1482205Notes

Reaction equation

HRID 1482205 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].[NH2:8][C@@H:9]([CH2:13][S:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]([OH:12])=[O:11].C(=O)([O-])[O-].[Na+].[Na+].Cl>O1CCCC1.O>[C:1]([NH:8][C@@H:9]([CH2:13][S:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10]([OH:12])=[O:11])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 76044S-Trityl-L-CysteineHCID 42284934-Pentenoyl chloride

Product 1

HCID 89668253HCID 89668253, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pent-4-enoyl chloride (0.915 ml, 8.25 mmol) was added to a solution of (R)-2-amino-3-(tritylthio)propanoic acid (1.50 g, 4.13 mmol) and sodium carbonate (1.31 g, 12.4 mmol) in tetrahydrofuran (3.5 ml) and water (7 ml), and the mixture was stirred at room temperature for one hour. The reaction mixture was then adjusted to pH 2 by adding concentrated hydrochloric acid thereto at 0° C. After dilution with ethyl acetate, salting-out extraction was carried out by adding an appropriate amount of NaCl. The resulting organic extract was washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→0/100) to afford (R)-2-(pent-4-enamido)-3-(tritylthio)propanoic acid (Compound 2h) (1.14 g, 62%).

Workup

  1. customat 0° C
  2. extractionAfter dilution with ethyl acetate, salting-out extraction
  3. additionby adding an appropriate amount of NaCl
  4. extractionThe resulting organic extract
  5. washwas washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→0/100)

Sources & evidence

ORD record
ord-1a8b9d0ec8fd4963a56259995e171bf4
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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