Hydrochloric Acid → HCID 131734148, compound

HRID 716673Notes

Reaction equation

HRID 716673 reaction equation
C(OC([NH:8][C@@H:9]([CH:24]([CH3:26])[CH3:25])[C:10]([S:12][CH2:13][C@H:14]([NH:20][C:21](=[O:23])[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:11])=O)(C)(C)C.[ClH:27]>O1CCOCC1>[ClH:27].[NH2:8][C@@H:9]([CH:24]([CH3:25])[CH3:26])[C:10]([S:12][CH2:13][C@H:14]([NH:20][C:21](=[O:23])[CH3:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118527161HCID 118527161, compound

Product 1

HCID 131734148HCID 131734148, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

ethyl (2R)-3-{[(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-methylbutanoyl]sulfanyl}-2-acetamidopropanoate (570 mg) was dissolved in a solution of hydrogen chloride (4N) in 1,4-dioxane (15 mL) and the reaction was stirred for 5 hours. The reaction mixture was concentrated at reduced pressure, triturated with ethyl acetate (15 mL) for 1 hour, filtered and dried to give the product as a white solid (430 mg, 90%). 1H NMR (300 MHz, DMSO) δ=8.63-8.48 (m, 4H), 4.41 (dt, J=5.3, 8.4 Hz, 1H), 4.17-4.04 (m, 4H), 3.55-3.45 (m, 2H), 3.12 (dd, J=8.6, 13.6 Hz, 1H), 2.17 (dt, J=5.0, 6.9 Hz, 1H), 1.83 (s, 3H), 1.21-1.15 (m, 3H), 0.96 (d, J=7.0 Hz, 3H), 0.93 (d, J=7.0 Hz, 3H). MS (ESI) m/z 291 (M+1)′.

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. customtriturated with ethyl acetate (15 mL) for 1 hour
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-a8a19670ce094a85b22bd2ea0215cfe3
Source dataset
uspto-grants-2015_11
Patent number
US09193681B1

Reaction notes

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