Lithium Hydroxide → 1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-[1'-phenyl-1'-carboxymethoxy]-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 458909Notes

Reaction equation

HRID 458909 reaction equation
[OH-].[Li+].[O:3]=[S:4]1(=[O:41])[C:10]2[CH:11]=[C:12]([O:16][CH:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18]([O:20]CC)=[O:19])[C:13]([Br:15])=[CH:14][C:9]=2[N:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:7][C:6]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:35][CH3:36])[CH2:5]1>C1COCC1.O>[O:41]=[S:4]1(=[O:3])[C:10]2[CH:11]=[C:12]([O:16][CH:17]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18]([OH:20])=[O:19])[C:13]([Br:15])=[CH:14][C:9]=2[N:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:7][C:6]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:35][CH3:36])[CH2:5]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 184424591,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-[1'-phenyl-1'-ethoxycarbonylmethoxy]-2,3,4,5-tetrahydro-1,5-benzothiazepine

Product 1

HCID 184424581,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-[1'-phenyl-1'-carboxymethoxy]-2,3,4,5-tetrahydro-1,5-benzothiazepineYield 92.3%

Reagents, catalysts & solvents 1

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

Procedure

Lithium hydroxide (0.019 g) was added to a solution of 1,1-dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-[1′-phenyl-1′-ethoxycarbonylmethoxy]-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 3; 0.244 g, 0.397 mmol) in THF/H2O (2/1, 3 ml). After 2 days the solvent was removed under reduced pressure and the crude mixture was purified by HPLC to give the title compound 0.215 g (92%) as a white solid. NMR (CD3OD) 0.60–0.80 (m, 6H), 0.90–1.25 (m, 4H), 1.30–1.60 (m, 4H), 3.05–3.30 (m, 2H), 3.40–3.90 (m, 2H), 5.55 (s, 1H), 6.85–7.70 (m, 12H).

Workup

  1. customAfter 2 days the solvent was removed under reduced pressure
  2. customthe crude mixture was purified by HPLC

Sources & evidence

ORD record
ord-3eb9d39de211488891b00468cb4a22f3
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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