Lithium Hydroxide → HCID 69584358, compound

HRID 1824423Notes

Reaction equation

HRID 1824423 reaction equation
COC(C1[N:9]2[C:10](=O)[CH2:11][CH2:12][CH:13]=[CH:14]C[CH:8]2[CH:7]([NH:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][N:21]=2)=O)C1)=O.[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1.[OH2:35].[OH-:36].[Li+].C(OCC)(=[O:40])C>>[C:20]1([C:18]([NH:17][C@@H:7]2[C:8](=[O:36])[N:9]3[C@H:31]([C:32]([OH:40])=[O:33])[CH2:30][CH2:34][C@H:10]3[CH2:11][CH:12]=[CH:13][CH2:14]2)=[O:35])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][N:21]=1

Participants

5

Reactant 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 21881883Oxolane--water (1/1)HCID 77688882HCID 77688882, compound

Product 1

HCID 69584358HCID 69584358, compoundYield 90%

Procedure

[(Isoquinoline-1-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester, 13, (1.62 g, 4.1 mmol) are added to 20 mL of THF/H2O (3:1). Lithium hydroxide (0.25 g) is added and the reaction stirred at room temperature for 18 hours then diluted with ethyl acetate (100 mL). The organic layer is washed with 1N HCl, brine, and dried over MgSO4. Solvent is removed in vacuo to afford 1.41 g (90% yield of the desired product as an oil, which is used without further purification. 1H NMR (CDCl3): δ 9.30 (d, J=8.5 Hz, 1H), 8.92 (d, J=7.7 Hz, 1H), 8.53 (d, J=7.8 Hz, 1H), 7.93 (m, 2H), 7.83–7.71 (m, 2H), 5.88 (m, 1H), 5.75 (m, 1H), 5.50 (m, 1H), 4.70 (d, 7.4 Hz, 1H), 4.37 (m, 1H), 3.10–2.91 (m, 2H), 2.44 (m, 3H), 2.21 (m, 1H), 2.03 (m, 2H), 13C NMR (CDCl3): δ 173.5, 171.9, 165.0, 148.1, 139.3, 137.9, 137.6, 131.7, 129.8, 129.5, 127.7, 127.3, 126.9, 125.9, 125.2, 61.4, 59.5, 50.9, 33.9, 33.3, 32.5, 26.0. ESI MS 380.15(M+H).

Workup

  1. washThe organic layer is washed with 1N HCl, brine
  2. dry with materialdried over MgSO4
  3. customSolvent is removed in vacuo

Sources & evidence

ORD record
ord-635b5110029f4f47be978083ab7c8960
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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