Acetic Acid → HCID 22393132, compound

HRID 1071307Notes

Reaction equation

HRID 1071307 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 45; 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 (400 MHz, 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),

Workup

  1. customwas removed under reduced pressure
  2. customThe crude product was purified by HPLC (MeCN)

Sources & evidence

ORD record
ord-2670f0c6313347eb9ac670a2c401eff5
Source dataset
uspto-grants-2005_06
Patent number
US06906058B2

Reaction notes

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