Hydrochloric Acid → HCID 68818301, compound

HRID 2112420Notes

Reaction equation

HRID 2112420 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:13][SH:14])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CCN(C(C)C)C(C)C.[Na+].[I-].[CH2:27](Br)[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].Cl>CC#N.O>[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:13][S:14][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 6259Phenacyl bromideHCID 81531DiisopropylethylamineHCID 10977409N-(tert-Butoxycarbonyl)-L-cysteine methyl ester

Product 1

HCID 68818301HCID 68818301, compoundYield 124.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of the N-Boc cysteine methyl ester (2.05 ml, 9.93 mmol) in MeCN (20 ml) at 0° C. were added DIPEA (3.55 ml, 20.1 mmol), NaI (0.48 g, 3.20 mmol), and then a solution of phenacyl bromide (2.41 g, 12.1 mmol) in MeCN (4 ml). The mixture was stirred at room temperature for 19 h. Water (100 ml) and 1N aqueous HCl. (30 ml) was added, and the product was extracted (3×AcOEt). The combined extracts were washed with brine, dried (MgSO4), and concentrated under reduced pressure to yield 4.37 g of an oil. Crystallization from AcOEt (approx 10 ml) and heptane (approx 40 ml) at −20° C. overnight yielded 3.49 g (99%) of the title methyl ester as a brown solid.

Workup

  1. addition(30 ml) was added
  2. extractionthe product was extracted (3×AcOEt)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-16987c89b4b64dc2b2b4ae4155adbe20
Source dataset
uspto-grants-2009_04
Patent number
US07524813B2

Reaction notes

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