Lithium Hydroxide → HCID 18442475, compound

HRID 458920Notes

Reaction equation

HRID 458920 reaction equation
[O:1]=[S:2]1(=[O:36])[C:8]2[CH:9]=[C:10]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:12][C:7]=2[N:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:5][C:4]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:30][CH3:31])[CH2:3]1.C1COCC1.[Li+].[OH-]>C(Cl)Cl.O.C(O)(=O)C>[O:36]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:17][CH2:18][C:19]([OH:21])=[O:20])[C:11]([S:13]([CH3:16])(=[O:14])=[O:15])=[CH:12][C:7]=2[N:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:5][C:4]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:30][CH3:31])[CH2:3]1

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 18442476HCID 18442476, compound

Product 1

HCID 18442475HCID 18442475, compoundYield 92.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 1,1-dioxo-3-butyl-3-ethyl-5-phenyl-7-mesyl-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 20; 46 mg, 0.085 mmol) was added THF (5 ml), water (1 ml) and LiOH (10 mg, 0.4 mmol). The reaction was stirred for 1 hour and then excess acetic acid was added to quench the reaction. Water and DCM were added and the aqueous phase was extracted three times with DCM. The combined organic phases were dried and concentrated to give the title compound 40 mg (91%). NMR 0.7–0.85 (m, 6H), 1.0–1.7 (m, 8H), 3.2 (m, 2H), 3.3 (s, 3H), 3.8 (s, 2H), 4.9 (s, 2H), 5.0 (brs, 1H), 7.05–7.15 (m, 3H), 7.3–7.4 (t, 2H), 7.5 (s; 1H), 7.6 (s, 1H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe aqueous phase was extracted three times with DCM
  4. customThe combined organic phases were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d0846c2b5e5a436a8531e065d9df9ba6
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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