(Diethylamino)sulfur trifluoride → HCID 57889143, compound

HRID 1016204Notes

Reaction equation

HRID 1016204 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2(O)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C@H:15]([NH:19][C:20]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:29])[CH3:28])=[CH:4][CH:3]=1.CCN(S(F)(F)[F:37])CC>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([F:37])[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C@H:15]([NH:19][C:20]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:29])[CH3:28])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluoride3×HCID 57889423HCID 57889423, compound

Product 1

HCID 57889143HCID 57889143, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

N—((R)-1-((S)-4-(4-Chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)cyclopentanecarboxamide (30 mg, 0.069 mmol) was dissolved into methylene chloride (2 mL) then cooled to −78° C. and DAST (13.3 mg, 0.083 mmol) was added. The reaction was stirred overnight at rt. HPLC showed some starting material present and 2 additional drops of DAST was added at rt. Some starting material was still present and 2 additional drops DAST was added and HPLC then showed the reaction was complete. The reaction was concentrated and Example 616 was isolated as a white solid by preparative reverse-phase HPLC (15.3 mg, 51% yield), M+H=437.38.

Workup

  1. concentrationThe reaction was concentrated
  2. customExample 616 was isolated as a white solid by preparative reverse-phase HPLC (15.3 mg, 51% yield), M+H=437.38

Sources & evidence

ORD record
ord-ef9ea8c4099541bab406a93839392da0
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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