Hydrochloric Acid → HCID 67404573, compound

HRID 1879265Notes

Reaction equation

HRID 1879265 reaction equation
C(OC([NH:8][C@@H:9]([CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[C:10]([N:12]1[CH2:20][C@H:19]([O:21][CH2:22][C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=[CH2:36])[CH:30]=3)[CH:26]=[CH:27][CH:28]=2)[CH2:18][C@H:13]1[C:14]([O:16][CH3:17])=[O:15])=[O:11])=O)(C)(C)C.[ClH:43]>O1CCOCC1>[ClH:43].[NH2:8][C@@H:9]([CH:37]1[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1)[C:10]([N:12]1[CH2:20][C@H:19]([O:21][CH2:22][C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=[CH2:36])[CH:30]=3)[CH:26]=[CH:27][CH:28]=2)[CH2:18][C@H:13]1[C:14]([O:16][CH3:17])=[O:15])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58005157HCID 58005157, compound

Product 1

HCID 67404573HCID 67404573, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl (4R)-1-{(2S)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylacetyl}-4-[(3′-vinylbiphenyl-3-yl)methoxy]-L-prolinate 107 was suspended in 4M solution of HCl in dioxane (final conc. 1.3 M) and stirred at RT for 2 h. The solvent was removed under reduced pressure, the residue was taken up with Et2O and evaporated to dryness to afford the title compound 108 (95% crude yield) as a white foam. 1H NMR (400 MHz, DMSO-d6, 300 K) δ 8.15 (bs, 3H), 7.46 (s, 1H), 7.72-7.64 (m, 2H), 7.60 (d, J 7.6, 1H), 7.57-7.46 (m, 3H), 7.40 (d, J 7.6, 1H), 6.87 (dd, J 17.7, 11.1, 1H), 5.98 (d, J 17.7, 1H), 5.37 (d, J 11.1, 1H), 4.65 (s, 2H), 4.46 (t, J 8.5, 1H), 4.36 (bs, 1H), 4.25-4.18 (m, 1H), 4.10 (d, J 11.4, 1H), 3.72-3.65 (m, 1H), 3.68 (s, 3H), 2.60-2.55 (m, partially obscured by residual DMSO-d6, 1H), 2.11-2.00 (m, 1H), 1.89-1.61 (m, 6H), 1.32-1.02 (m, 5H). MS (ES+) m/z 477 (M+H)+

Workup

  1. customThe solvent was removed under reduced pressure
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-0749ffbf321648839ee0eab23210b57c
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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