Acetic Acid → HCID 22393108, compound

HRID 458915Notes

Reaction equation

HRID 458915 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]([O: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.[OH-].[Na+].C(O)(=O)C>C(O)C.O>[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]([O: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

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 22393120HCID 22393120, compound

Product 1

HCID 22393108HCID 22393108, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-methoxy-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 7; 1.2 g) was dissolved in ethanol (20 ml). Sodium hydroxide (0.5) dissolved in H2O (1 ml) was added and the reaction mixture was warmed to 40° C. for 30 min. Acetic acid (1 ml) was added and the solvent was removed at reduced pressure. The residue was partitioned between DCM/H2O and the organic layer was separated and dried. Trituration of the residue with n-hexane gave the title compound 1.1 g (97%) as a solid. NMR 0.75–0.85 (m, 3H), 0.9 (t, 3H), 1.0–1.7 (m, 8H), 3.2 (q, 2H), 3.65 (s, 3H), 3.65–3.85 (m, 2H), 4.7 (s, 2H), 6.4 (s, 1H), 7.0 (t, 1H), 7.1 (d, 2H), 7.3 (t, 2H), 7.5 (s, 1H).

Workup

  1. additionwas added
  2. customthe solvent was removed at reduced pressure
  3. customThe residue was partitioned between DCM/H2O
  4. customthe organic layer was separated
  5. customdried

Sources & evidence

ORD record
ord-841c3335052245dca3c850cd698643fa
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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