Hydrochloric Acid → HCID 86622986, compound

HRID 2233798Notes

Reaction equation

HRID 2233798 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:22]C(OC(C)(C)C)=O)[C:11]([O:13][C@H:14]([CH3:21])[C@H:15]([O:17][C:18](=[O:20])[CH3:19])[CH3:16])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[ClH:30]>O1CCOCC1>[ClH:30].[NH2:22][C@@H:10]([CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=1)[C:11]([O:13][C@H:14]([CH3:21])[C@H:15]([O:17][C:18](=[O:20])[CH3:19])[CH3:16])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86621601HCID 86621601, compound

Product 1

HCID 86622986HCID 86622986, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1R,2R)-2-Acetyloxy-1-methylpropyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate (8) (0.4 g, 0.97 mmol) was dissolved in 8 mL of 4M HCl in 1,4-dioxane. The resulting mixture was stirred at room temperature for 60 min. After removing dioxane, acetonitrile (5 mL) was added. The title compound (5) (0.16 g, 53% yield) was crystallized and collected by filtration. 1H NMR (400 MHz, CD3OD): δ 1.19 (d, J=6.4 Hz, 3H), 1.21 (d, J=6.4 Hz, 3H), 2.04 (s, 3H), 3.02 (dd, J=12.0, 6.4 Hz, 1H), 3.07 (dd, J=12.0, 6.4 Hz, 1H), 4.21 (t, J=6.4 Hz, 1H), 4.95 (m, 1H), 5.04 (m, 1H), 6.57 (dd, J=8.0, 2.0 Hz, 1H), 6.67 (d, J=2.0 Hz, 1H), 6.74 (d, J=8.0 Hz, 1H). MS (ESI) m/z 312.2 (M+H)+ and 310.2 (M−H)−.

Workup

  1. customAfter removing dioxane, acetonitrile (5 mL)
  2. additionwas added

Sources & evidence

ORD record
ord-7dcf0c9c24ac48c8b82e619bb9855030
Source dataset
uspto-grants-2010_05
Patent number
US07709527B2

Reaction notes

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