Trifluoroacetic acid → HCID 67433636, compound

HRID 74857Notes

Reaction equation

HRID 74857 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][CH:18]([O:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][CH:18]([O:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86658293tert-Butyl 2-(cholestan-3-yloxy)acetate

Product 1

HCID 67433636HCID 67433636, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(cholestan-3-yloxy)acetate 129 (634 mg, 1.26 mmol) was taken up in DCM (4 mL) before TFA (1 mL) was added. The solution was stirred at room temperature for 90 mins. The solvent was evaporated and the residue purified using a short silica plug (SiO2: DCM to 100:5 DCM:MeOH) before being recrystallized from hexane to yield 439 mg of the white solid product (78%). 1H nmr (400 MHz, CDCl3) δ: 4.25 (s, 2H, CH2O), 3.37 (m, 1H, CHO), 1.99-0.58 (m, 31H), 0.89 (d, 3H, J=6.6, CH3), 0.85 (d, 3H, J=2.0, CH3), 0.84 (d, 3H, J=1.4, CH3), 0.80 (s, 3H, CH3), 0.64 (s, 3H, CH3).

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe residue purified
  4. custombefore being recrystallized from hexane

Sources & evidence

ORD record
ord-a4656bb8e7d34cb5a8df1b1f89428010
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

Loading…