Hydrochloric Acid → HCID 25067090, compound

HRID 1171247Notes

Reaction equation

HRID 1171247 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:8]=[C:9]([CH2:19][C@H:20]([NH:32]C(OC(C)(C)C)=O)[C:21]([O:23][C@H:24]([CH3:31])[C@H:25]([O:27][C:28](=[O:30])[CH3:29])[CH3:26])=[O:22])[CH:10]=[CH:11][C:12]=1[O:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2].[ClH:40]>O1CCOCC1>[ClH:40].[NH2:32][C@@H:20]([CH2:19][C:9]1[CH:10]=[CH:11][C:12]([O:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]([O:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:8]=1)[C:21]([O:23][C@H:24]([CH3:31])[C@H:25]([O:27][C:28](=[O:30])[CH3:29])[CH3:26])=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86621602HCID 86621602, compound

Product 1

HCID 25067090HCID 25067090, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1R,2R)-2-Acetyloxy-1-methylpropyl(2S)-3-[3,4-bis(ethoxycarbonyloxy)phenyl]-2-[(tert-butoxy)carbonylamino]propanoate (35) (0.6 g, 1.1 mmol) was dissolved in 10 mL of 4M HCl in 1,4-dioxane. The mixture was stirred at room temperature for 60 min. Dioxane was evaporated under reduced pressure. The colorless oil was further dried under vacuum to give 0.6 g (96% yield) of the title compound (31). 1H NMR (400 MHz, CD3OD): δ 1.16 (d, J=7.8 Hz, 3H), 1.18 (d, J=7.8 Hz, 3H), 1.35 (t, J=7.2 Hz, 3H), 1.36 (t, J=7.2 Hz, 3H), 2.03 (s, 3H), 3.23 (dd, J=14.0, 6.8 Hz, 1H), 3.27 (dd, J=14.0, 6.8 Hz, 1H), 4.28 (q, J=7.2 Hz, 2H), 4.30 (q, J=7.2 Hz, 2H), 4.40 (t, J=6.8 Hz, 1H), 4.94 (m, 1H), 5.05 (m, 1H), 7.26 (dd, J=8.0, 2.0 Hz, 1H), 7.30 (d, J=2.0 Hz, 1H), 7.33 (d, J=8.0 Hz, 1H). MS (ESI) m/z 456.2 (M+H)+ and 454.0 (M−H)−.

Workup

  1. customDioxane was evaporated under reduced pressure
  2. customThe colorless oil was further dried under vacuum

Sources & evidence

ORD record
ord-ad50465680e24f88b6898852da10ce0c
Source dataset
uspto-grants-2010_11
Patent number
US07829592B2

Reaction notes

Loading…