HCID 21896694, compound → HCID 21896664, compound

HRID 719102Notes

Reaction equation

HRID 719102 reaction equation
[O:1]=[S:2]1(=[O:47])[C:8]2[CH:9]=[C:10]([O:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:5][C:4]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:30][CH2:31][CH2:32][CH3:33])[N:3]1CC1C=CC(OC)=CC=1>C(O)(C(F)(F)F)=O>[O:47]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:15][CH2:16][C:17]([OH:19])=[O:18])[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:5][C:4]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:30][CH2:31][CH2:32][CH3:33])[NH:3]1

Participants

3

Reactant 1

HCID 21896694HCID 21896694, compound

Product 1

HCID 21896664HCID 21896664, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dioxo-2-(4-methoxybenzyl)-3,3-dibutyl-5-phenyl-7-methylthio-8-(t-butoxycarbonylmethoxy)-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine (Method 25; 6.902 g, 10.11 mmol) was dissolved in a mixture of TFA (50 ml) and Et3Si (8 ml) and the solution was stirred for 90 min at RT. The solvent was removed under reduced pressure and the residue was dissolved in t-BuOMe (100 ml). The organic phase was washed with water (20 ml) and then extracted three times with diluted NaOH (2×50 ml 0.5M). The combined aqueous extracts were acidified with diluted HCl (70 ml, 1M) (pH 1–2) and were then extracted twice with t-BuOMe (2×50 ml). The ether layer was washed with brine, dried over MgSO4 and concentrated. 4.694 g (92%) of the desire product as brown oil were obtained. NMR (400 MHz, CD3OD): 0.70–0.85 (m, 6H), 1.00–1.25 (m, 6H), 1.25–1.50 (m, 4H), 1.55–1.70 (m 2H), 2.10 (s, 3H), 3.90 (brs, 2H), 4.55 (s, 2H), 6.60 (s, 1H), 6.95–7.35 (m, 6H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in t-BuOMe (100 ml)
  3. washThe organic phase was washed with water (20 ml)
  4. extractionextracted three times with diluted NaOH (2×50 ml 0.5M)
  5. extractionwere then extracted twice with t-BuOMe (2×50 ml)
  6. washThe ether layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bb6e399b25fb46419525b3fc11c45f4b
Source dataset
uspto-grants-2006_11
Patent number
US07132416B2

Reaction notes

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