Acetic Acid → HCID 18442440, compound

HRID 458517Notes

Reaction equation

HRID 458517 reaction equation
[O:1]=[S:2]1(=[O:33])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][C:16]([OH:18])=[O:17])[C:11](Br)=[CH:12][C:7]=2[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5][C:4]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3]1.[CH3:34][S-:35].[Na+].C(O)(=O)C>CN(C=O)C>[O:1]=[S:2]1(=[O:33])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][C:16]([OH:18])=[O:17])[C:11]([S:35][CH3:34])=[CH:12][C:7]=2[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5][C:4]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4378561Sodium methanethiolateHCID 22393109HCID 22393109, compound

Product 1

HCID 18442440HCID 18442440, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1,1-Dioxo-3,3-dibutyl-5-phenyl-7-bromo-8-carboxymethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 11; 500 mg, 0.93 mmol) was dissolved in DMF (10 ml). Sodium methanethiolate (200 mg, 2.85 mmol) was added and the mixture was stirred for 2 hours at 50° C. Acetic acid (0.4 ml) was added and the solvent was evaporated under reduced pressure. The residue was extracted with EtOAc/water. The EtOAc layer was separated, dried and evaporated under reduced pressure to give the title compound 450 mg (96%). NMR (300 MHz) 0.7–0.8 (m, 6H), 1.0–1.6 (m, 12H), 2.2 (s, 2H), 3.2 (brs, 2H), 3.7 (brs, 2H), 4.8 (s, 2H), 6.6 (s, 1H), 6.9–7.1 (m, 3H), 7.2–7.4 (m, 3H).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. extractionThe residue was extracted with EtOAc/water
  3. customThe EtOAc layer was separated
  4. customdried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fd0c99499f8447d4a1e306bdd91f42bb
Source dataset
uspto-grants-2007_03
Patent number
US07192946B2

Reaction notes

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