Hydrochloric Acid → HCID 60209722, compound

HRID 2264147Notes

Reaction equation

HRID 2264147 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([N:16]([CH2:21][C:22]2[CH:32]=[CH:31][C:25]3[O:26][CH2:27][CH2:28][CH2:29][O:30][C:24]=3[CH:23]=2)[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:9]1)C1C=CC=CC=1.Cl>O1CCOCC1>[O:26]1[C:25]2[CH:31]=[CH:32][C:22]([CH2:21][N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([C@@H:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[O:15])=[CH:23][C:24]=2[O:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16122905HCID 16122905, compound

Product 1

HCID 60209722HCID 60209722, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8.79 g of (−)-4-benzyl-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylmorpholine-2-carboxamide and 50 mL of 4N HCl in dioxane was stirred for 3 hrs at room temperature, then concentrated under reduced pressure. The residue was partitioned between 3×50 mL of chloroform and 20 mL of saturated sodium carbonate, dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum gave the product as a resin: MS (m+1)=349.3; H NMR (400 MHz, CDCl3) 7.3-6.7 (complex m, 5H), 4.6 (br d, 1H), 6.8-6.7 (m, 2H), 4.4 (d, 1H), 4.2 (m, 4H), 4.15 (q, 1H), 4.08 (br d, 1H), 3.95 (m, 1H), 3.5 (m, 1H), 3.2 (m, 1H), 3.0 (dd, 1H), 2.2 (m, 1H), 2.0 (m, 1H) 1.45 (2×s, 9H), 0.9 (dd, 6H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between 3×50 mL of chloroform and 20 mL of saturated sodium carbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customDrying under vacuum
  6. customgave the product as a resin

Sources & evidence

ORD record
ord-240728fbe4ed451eb2794ead2215b599
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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