Hydrochloric Acid → HCID 66673333, compound

HRID 2369193Notes

Reaction equation

HRID 2369193 reaction equation
C1([C@H](OC(=O)[NH:11][C@H:12]2[C@H:21]([O:22][CH3:23])[CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:24](=[O:26])[NH2:25])=[CH:17][CH:18]=3)[C:13]2([CH2:29][CH3:30])[CH2:27][CH3:28])C)C=CC=CC=1.Cl.O1CCOCC1>>[NH2:11][C@@H:12]1[C:13]([CH2:27][CH3:28])([CH2:29][CH3:30])[C:14]2[CH:15]=[C:16]([C:24]([NH2:25])=[O:26])[CH:17]=[CH:18][C:19]=2[CH2:20][C@H:21]1[O:22][CH3:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66701949HCID 66701949, compound

Product 1

HCID 66673333HCID 66673333, compound

Procedure

((2R,3R)-7-Carbamoyl-1,1-diethyl-3-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid (R)-1-phenyl-ethyl ester (1.7 g, 4.0 mmol) was treated with 4.0 N HCl in dioxane (20 mL, 80 mmol) and stirred at RT. After 24 h, the solvent was removed at reduced pressure and the residual solid was triturated with 50% dichloromethane in hexane (15 mL). The solid was collected on a Buchner funnel, rinsed with 50% dichloromethane in hexane (10 mL) and dried under vacuum to give the title compound as the hydrochloride salt (1.2 g). (m/z): [M+H]+ calcd for C16H24N2O2 277.19; found 277.4. 1H NMR (d6-DMSO, 400 mHz) δ (ppm) 8.19 (br s, 3H), 7.98 (s, 1H), 7.70 (m, 2H), 7.32 (s, 1H) 7.19 (d, J=7.8 Hz, 1H), 3.83 (m, 1H), 3.47 (m, 1H), 3.42 (s, 3H), 3.23 (m, 1H), 2.63 (dd, J=16.8 Hz, 9.7 Hz, 1H) 2.06 (m, 1H), 1.88 (m, 1H) 1.64 (guar, J=7.7 Hz, 2H), 0.62 (t, J=7.5 Hz, 3H), 0.50 (t, J=7.0 Hz, 3H).

Workup

  1. customthe solvent was removed at reduced pressure
  2. customthe residual solid was triturated with 50% dichloromethane in hexane (15 mL)
  3. customThe solid was collected on a Buchner funnel
  4. washrinsed with 50% dichloromethane in hexane (10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2728d9ce2229470bb23de92a718ea990
Source dataset
uspto-grants-2014_04
Patent number
US08703791B2

Reaction notes

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