Hydrochloric Acid → HCID 69019103, compound

HRID 1772387Notes

Reaction equation

HRID 1772387 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@H:13]([O:19][CH3:20])[C@@H:14]([CH3:18])[C:15]([OH:17])=[O:16])=O)(C)(C)C.[ClH:21].O1CCOCC1>COC1CCCC1>[ClH:21].[CH3:20][O:19][C@@H:13]([C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[C@@H:14]([CH3:18])[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11033491(2R,3R)-3-((2S)-1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoic acid

Product 1

HCID 69019103HCID 69019103, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 138539Cyclopentyl methyl etherSolvent

Procedure

To a mixture of #11 (4.09 g, 14.2 mmol, 1 eq.) in cyclopentyl methyl ether (10 mL, 0.14 M) was added a 4 N solution of hydrogen chloride in dioxane (37 mL, 100 mmol, 7 eq.). After three hours, the reaction mixture was concentrated in vacuo and azeotroped three times with heptane to give #103 (1000 mg, 31%) as a gum, which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.92-10.06 (br s, 1H), 8.66-8.80 (br s, 1H), 3.89 (dd, J=5.2, 4.9 Hz, 1H), 3.43-3.53 (m, 1H), 3.39 (s, 3H), 3.06-3.17 (m, 2H), 2.66 (qd, J=7.1, 4.6 Hz, 1H), 1.71-2.03 (m, 4H), 1.11 (d, J=7.1 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customazeotroped three times with heptane

Sources & evidence

ORD record
ord-ff8c4de475054ba29c38bc28cc604f2b
Source dataset
uspto-grants-2016_02
Patent number
US09249186B2

Reaction notes

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