Lithium Hydroxide → HCID 22393115, compound

HRID 1071305Notes

Reaction equation

HRID 1071305 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]C)=[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.[CH2:35]1COC[CH2:36]1.[Li+].[OH-]>C(Cl)Cl.O.CC(O)=O>[O:1]=[S:2]1(=[O:34])[C:8]2[CH:9]=[C:10]([O:15][CH2:16][C:17]([OH:19])=[O:18])[C:11]([S:13][CH2:35][CH3:36])=[CH:12][C:7]=2[N:6]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=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 22393115HCID 22393115, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-methylthio-8-ethoxycarbonylmethoxy-2,3,4,5 tetrahydro-1,5-benzothiazepine (Method 43; 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 AcOH (0.2 ml) was added along with water (10 ml) and DCM (10 ml) The aqueous layer was then extracted three times with DCM. The combined organic phases were then dried and concentrated to give the title compound 450 mg (99%). NMR (400 MHz) 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), 0-7.9 (m, 6H), 7.05 (d, 2H), 7.25 (t, 2H), 7.35 (s, 1H), 8.4 (brs, 1H).

Workup

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

Sources & evidence

ORD record
ord-593bc2509b574ffbaa7dc6d9bf4ced8a
Source dataset
uspto-grants-2005_06
Patent number
US06906058B2

Reaction notes

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