Lithium hydroxide, monohydrate → HCID 67026786, compound

HRID 2237635Notes

Reaction equation

HRID 2237635 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:36])[N:9]([C:13]3[CH:18]=[CH:17][C:16]([C@@H:19]4[CH2:26][CH2:25][C@H:24]5[C@@H:20]4[CH2:21][CH2:22][C@H:23]5[CH:27]([C:32]([O:34]C)=[O:33])[C:28]([O:30]C)=[O:29])=[CH:15][CH:14]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1.O.[OH-].[Li+]>O1CCOCC1.O>[NH2:1][C:2]1[C:7]2[C:8](=[O:36])[N:9]([C:13]3[CH:18]=[CH:17][C:16]([C@@H:19]4[CH2:26][CH2:25][C@H:24]5[C@@H:20]4[CH2:21][CH2:22][C@H:23]5[CH:27]([C:28]([OH:30])=[O:29])[C:32]([OH:34])=[O:33])=[CH:15][CH:14]=3)[CH2:10][CH2:11][O:12][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67026968HCID 67026968, compound

Product 1

HCID 67026786HCID 67026786, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

(±)-{(1R,3aS,4R,6aS)-4-[4-(4-Amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)phenyl]octahydropentalen-1-yl}malonic acid was prepared as follows. A solution of dimethyl(±)-{(1R,3aS,4R,6aS)-4-[4-(4-amino-5-oxo-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-6(5H)-yl)phenyl]octahydropentalen-1-yl}malonate (190 mg, 0.38 mmol) and lithium hydroxide monohydrate (166 mg, 3.9 mmol) in p-dioxane/water (8:3-11 mL) was stirred at 50° C. for 3 hours. The reaction was concentrated to remove the p-dioxane, water (2 mL) added and the mixture extracted with EtOAc (5 mL). The aqueous layer was adjusted to pH˜3 with 2N aqueous hydrochloric acid, the solids filtered and dried in vacuo to afford the title compound as a white solid, 179 mg. 1H NMR (400 MHz, DMSO-d6) δ 8.17 (s, 1H), 7.58 (br s, 2H), 7.13 (d, 2H), 7.10 (d, 2H), 4.57 (m, 2H), 3.95 (m, 2H), 3.08 (d, 1H), 2.64 (m, 1H), 2.39 (m, 2H), 2.24 (m, 1H), 1.87-1.10 (m, 7H). m/z=467.3 (M+1).

Workup

  1. concentrationThe reaction was concentrated
  2. customto remove the p-dioxane, water (2 mL)
  3. additionadded
  4. extractionthe mixture extracted with EtOAc (5 mL)
  5. filtrationthe solids filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1ae8704f5dfc4021b5335d47dce17a82
Source dataset
uspto-grants-2010_05
Patent number
US07718645B2

Reaction notes

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