(Diethylamino)sulfur trifluoride → HCID 178442394, compound

HRID 1675557Notes

Reaction equation

HRID 1675557 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-4f8f1c9b464740878a0d41652ff39380
Source dataset
uspto-grants-2011_08
Patent number
US08003685B2

Reaction notes

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