Acetic Acid → HCID 22393132, compound

HRID 458911Notes

Reaction equation

HRID 458911 reaction equation
[OH-].[Li+].[O:3]=[S:4]1(=[O:38])[C:10]2[CH:11]=[C:12]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])[C:13]([O:15][CH3:16])=[CH:14][C:9]=2[N:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:7][C:6]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:5]1.CC(O)=O>C1COCC1.O>[O:38]=[S:4]1(=[O:3])[C:10]2[CH:11]=[C:12]([O:17][CH2:18][C:19]([OH:21])=[O:20])[C:13]([O:15][CH3:16])=[CH:14][C:9]=2[N:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:7][C:6]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:5]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 22393105HCID 22393105, compound

Product 1

HCID 22393132HCID 22393132, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (0.062 g) was added to a solution of 1,1-dioxo-3,3-dibutyl-5-phenyl-7-methoxy-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 5; 0.448 g, 0.865 mmol) in THF/H2O (2/1, 6 ml) After 1 hour AcOH (0.5 ml) was added and most of the solvent was removed under reduced pressure. The crude product was purified by HPLC (MeCN) to give the title compound 0.408 g (96%) as a white solid. NMR (CD3OD) 0.75–0.85 (m, 6H), 1.00–1.30 (m, 8H), 1.35–1.55 (m, 4H), 3.20 (s, 2H), 3.65 (s, 3H), 3.70 (brs, 2H), 4.50 (s, 2H), 6.50 (s, 1H), 6.90–7.30 (m, 5H), 7.40 (s, 1H).

Workup

  1. additionwas added and most of the solvent
  2. customwas removed under reduced pressure
  3. customThe crude product was purified by HPLC (MeCN)

Sources & evidence

ORD record
ord-e5c324ed887344cfa4f4a3f691d2549d
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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