Hydrochloric Acid → HCID 69649774, compound

HRID 1914990Notes

Reaction equation

HRID 1914990 reaction equation
C(OC([NH:8][C:9]([CH3:34])([C:11]([O:13][C:14]1[C:15]([O:30][C:31](=[O:33])[CH3:32])=[C:16]2[C:21](=[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=13)[O:20][C:19]([CH3:29])([CH3:28])[CH2:18][CH2:17]2)=[O:12])[CH3:10])=O)(C)(C)C.[ClH:35]>O1CCOCC1>[ClH:35].[CH3:34][C:9]([C:11]([O:13][C:14]1[C:15]([O:30][C:31](=[O:33])[CH3:32])=[C:16]2[C:21](=[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=13)[O:20][C:19]([CH3:28])([CH3:29])[CH2:18][CH2:17]2)=[O:12])([CH3:10])[NH2:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58601388HCID 58601388, compound

Product 1

HCID 69649774HCID 69649774, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 5-(acetyloxy)-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromen-6-yl N-(tert-butoxycarbonyl)-2-methylalaninate (27) (0.4 g, 0.85 mmol) in 1,4-dioxane (5 mL) is added a solution of hydrogen chloride gas in anhydrous 1,4-dioxane (4.0 M, 10 mL). The reaction is stirred at room temperature for 2 hours. The reaction is dried under reduced pressure and the resulting solid is triturated with Et2O to afford the desired product as a white solid (0.388 g, 97%). M.p.=283-284° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.93 (br. s, 3H), 8.15 (d, J=8.4 Hz, 1H), 7.72 (d, J=8.0 Hz, 1H), 7.65-7.50 (m, 2H), 2.63 (t, J=6.6 Hz, 2H), 2.38 (s, 3H), 1.89 (t, J=6.6 Hz, 2H), 1.78 (s, 6H), 1.39 (s, 6H); LCMS: 372 [M+H]; Calc. for C21H25NO5.1.15 HCl: C, 60.96; H, 6.38; N, 3.39; Found C, 61.01; H, 6.06; N, 3.30.

Workup

  1. customThe reaction is dried under reduced pressure
  2. customthe resulting solid is triturated with Et2O

Sources & evidence

ORD record
ord-1e070482da07495c804f873a83bf8005
Source dataset
uspto-grants-2013_12
Patent number
US08614228B2

Reaction notes

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