(Diethylamino)sulfur trifluoride → HCID 178442394, compound

HRID 2388287Notes

Reaction equation

HRID 2388287 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([C@H:23]2[CH2:28][CH2:27][C@@H:26](O)[CH2:25][CH2:24]2)[C:14]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH3:22])[CH2:18][CH2:17]2)=[O:15])[CH:6]=1.C(N(S(F)(F)[F:38])CC)C>C(Cl)Cl.O>[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([C@H:23]2[CH2:28][CH2:27][C@H:26]([F:38])[CH2:25][CH2:24]2)[C:14]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH3:22])[CH2:18][CH2:17]2)=[O:15])[CH:6]=1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 178442399HCID 178442399, compound

Product 1

HCID 178442394HCID 178442394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 5-(3,3-dimethyl-but-1-ynyl)-3-[(cis-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (102 mg, 0.23 mmol) in dry CH2Cl2 (2 mL) is added DAST (Diethylaminosulphurtrifluoride) (90 μL, 0.69 mmol), and the mixture is stirred for 4 h at room temperature. Then it is diluted with CH2Cl2, water is added to the mixture, and it is vigorously stirred for 20 min. Organic fraction is separated, dried over Na2SO4, concentrated, and the residue is purified by preparative HPLC to give 5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-fluoro-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid.

Workup

  1. additionis added to the mixture, and it
  2. stirringis vigorously stirred for 20 min
  3. customOrganic fraction is separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-b8fda0813cbd4529824d6d526bdf9777
Source dataset
uspto-grants-2012_09
Patent number
US08269014B2

Reaction notes

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