Tetrabutylammonium Fluoride → HCID 145857714, compound

HRID 2216154Notes

Reaction equation

HRID 2216154 reaction equation
C[Si](C)(C)CCOC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([C:24]3[CH:28]=[C:27]([C:29]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[NH:30])[S:26][C:25]=3[S:39][CH3:40])(=[O:23])=[O:22])[CH:16]=2)=[C:10]([NH2:41])[CH:9]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:35]([O:34][C:32](=[O:33])[NH:31][C:29]([C:27]1[S:26][C:25]([S:39][CH3:40])=[C:24]([S:21]([C:17]2[CH:16]=[C:15]([C:11]3[C:12]([CH3:14])=[CH:13][C:8]([NH2:7])=[CH:9][C:10]=3[NH2:41])[CH:20]=[CH:19][CH:18]=2)(=[O:22])=[O:23])[CH:28]=1)=[NH:30])([CH3:37])([CH3:38])[CH3:36]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 145857641HCID 145857641, compound

Product 1

HCID 145857714HCID 145857714, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

{2-Amino-3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester (1000 mg, 1.48 mmol, Example 294, step f) was dissolved into THF (25 mL). To this was added TBAF (1M, 1.62 mL, 1.62 mmol) and the reaction was warmed to 40° C. with stirring for 3 hours. Additional TBAF (1.48 mL, 1.48 mmol) was added and the reaction was stirred at rt overnight. The solvents were removed in vacuo, the residue was dissolved into EtOAc and washed with water several times (5 washes). The combined organic layers were dried (MgSO4) and the solvents were removed in vacuo resulting in the title compound as a yellow solid (800 mg, 100%). 1H-NMR (CDCl3): δ: 8.03 (s, 1H), 7.95–7.93 (m, 1H), 7.89–7.88 (m, 1H), 7.59–7.53 (m, 2H), 6.08 (m, 1H), 5.99 (m, 1H), 2.55 (s, 3H), 1.85 (s, 3H), 1.52 (s, 9H).

Workup

  1. stirringthe reaction was stirred at rt overnight
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue was dissolved into EtOAc
  4. washwashed with water several times (5 washes)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-6343862bdcdf4c8eb9300f5da1c16ce7
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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