Trifluoroacetic acid → HCID 53240949, compound

HRID 422190Notes

Reaction equation

HRID 422190 reaction equation
[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:25])[C@H:15]([CH2:16][S:17]2(=[O:21])=[O:20])[C@:14]2([CH3:22])[C@H:9]([C:10]([CH3:24])([CH3:23])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[C:4]([C:26]([N:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)=[O:27])[CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:25])[C@H:15]([CH2:16][S:17]2(=[O:21])=[O:20])[C@:14]2([CH3:22])[C@H:9]([C:10]([CH3:23])([CH3:24])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[C:4]([C:26]([N:28]2[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]2)=[O:27])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86654197HCID 86654197, compound

Product 1

HCID 53240949HCID 53240949, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-{[(1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl]-carbonyl}piperazine-1-carboxylate (99) (0.13 g, 0.23 mmol) and trifluoroacetic acid (1.0 mL, 13 mmol) in CH2Cl2 (10 mL) was stirred at room temperature under N2 for 18 h. The mixture was concentrated under reduced pressure, and basified with Et3N, dissolved in EtOAc and washed with water. The organic layer was separated and concentrated to dryness under reduced pressure to give (1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-3-[(piperazin-1-yl)carbonyl]-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (100) (0.06 g, 55%) as a brown solid. 1H NMR (CD3OD): δ 7.27 (d, 1H), 6.78 (d, 1H), 3.50 (m, 3H), 3.02 (m 2H), 2.90 (m, 2H), 2.53 (m, 1H), 2.16 (d, 1H), 1.88-1.14 (m, 14H), 1.00 (m, 5H), 0.90 (s, 3H), 0.86 (s, 3H). MS m/z 475 (C26H38N2O4S+H+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in EtOAc
  3. washwashed with water
  4. customThe organic layer was separated
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a66e282fb3f24ec2ac99eba587dfaa95
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

Loading…