Trifluoroacetic acid → HCID 59267851, compound

HRID 553630Notes

Reaction equation

HRID 553630 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1[S:16][C:17]([C:20]([CH3:41])([CH3:40])[CH2:21][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:18][N:19]=1)(C)(C)C>C(Cl)Cl>[C:36]([Si:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:22][CH2:21][C:20]([C:17]1[S:16][C:15]([NH2:14])=[N:19][N:18]=1)([CH3:41])[CH3:40])([CH3:37])([CH3:38])[CH3:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59267969HCID 59267969, compound

Product 1

HCID 59267851HCID 59267851, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 10% solution of TFA in DCM (720 mL) is added at 0° C. to a solution of {5-[2-(tert-Butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-1,3,4-thiadiazol-2-yl}-carbamic acid tert-butyl ester (12.0 g, 23.4 mmol) in DCM (800 mL). The reaction mixture is stirred at room temperature for 14 h. The solvent is removed under reduced pressure and the crude purified by column chromatography to afford 8.8 g of 5-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-1,3,4-thiadiazol-2-ylamine as a viscous liquid. Yield: 91%; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.05 (9H, s), 1.30 (6H, s), 3.60 (2H, s), 7.30-7.50 (6H, m), 7.50-7.70 (4H, m), 9.00 (2H, s); m/z 412 [M+H].

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe crude purified by column chromatography

Sources & evidence

ORD record
ord-94da9b48ad9e4d1da52cbc85f300a9e0
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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