Lithium Hydroxide → HCID 17931372, compound

HRID 458919Notes

Reaction equation

HRID 458919 reaction equation
[O:1]=[S:2]1(=[O:34])[C:8]2[CH:9]=[C:10]([O:15][CH2:16][C:17]([O:19]CC)=[O:18])[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:5][C:4]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:28][CH3:29])[CH2:3]1.C1COCC1.[Li+].[OH-]>C(Cl)Cl.O.C(O)(=O)C>[O:34]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:15][CH2:16][C:17]([OH:19])=[O:18])[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:5][C:4]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:28][CH3:29])[CH2:3]1

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 22393123HCID 22393123, compound

Product 1

HCID 17931372HCID 17931372, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 1,1-dioxo-3-butyl-3-ethyl-5-phenyl-7-methylthio-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 16; 478 mg, 0.95 mmol) was added THF (15 ml), water (3 ml) and LiOH (34 mg, 1.4 mmol). The reaction was then stirred for 1 hour. Then acetic acid (0.2 ml) was added along with water (10 ml) and DCM (10 ml) The aqueous layer were then extracted three times with DCM. The combined organic phases were then dried and concentrated to give the title compound 450 mg (99%). NMR 0.7–0.9 (m, 6H), 1.0–1.7 (m, 8H), 2.2 (s, 3H), 3.2 (q, 2H), 3.7 (m, 2H), 4.8 (s, 2H), 6.65 (s, 1H), 6.95 (t, 1H), 7.05 (d, 2H), 7.25 (t, 2H), 7.35 (s, 1H), 8.4 (brs, 1H).

Workup

  1. extractionwere then extracted three times with DCM
  2. customThe combined organic phases were then dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-72ce575280064adaac63bbe35fbe89f4
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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