Triethylamine → HCID 71245517, compound

HRID 2369843Notes

Reaction equation

HRID 2369843 reaction equation
Cl.[F:2][C@@:3]12[C@:16]3([CH3:17])[C:11](=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]3)[C@@H:10]([F:19])[CH2:9][C@H:8]1[C@@H:7]1[CH2:20][C@@H:21]3[C@:25]([C:26](=[O:32])[CH2:27][O:28][C:29](=[O:31])[CH3:30])([C@@:6]1([CH3:33])[CH2:5][C@@H:4]2[OH:34])[CH2:24][NH:23][CH2:22]3.C(N(CC)CC)C.Cl[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH3:50])[CH:45]=1.CC1C=C(C=CC=1)CBr>C(Cl)Cl>[F:2][C@@:3]12[C@:16]3([CH3:17])[C:11](=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]3)[C@@H:10]([F:19])[CH2:9][C@H:8]1[C@@H:7]1[CH2:20][C@@H:21]3[C@:25]([C:26](=[O:32])[CH2:27][O:28][C:29](=[O:31])[CH3:30])([C@@:6]1([CH3:33])[CH2:5][C@@H:4]2[OH:34])[CH2:24][N:23]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH3:50])[CH:45]=1)[CH2:22]3

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 12099m-Xylyl bromideHCID 12102m-Xylyl chlorideHCID 67353702Acetic acid 2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4-aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester hydrochloride

Product 1

HCID 71245517HCID 71245517, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

In a nitrogen atmosphere, intermediate 6 (200 mg, 0.400 mmol) was dissolved in DCM (5 ml), triethylamine (166 μL, 1.20 mmol) and 1-(chloromethyl)-3-methylbenzene (79 μL, 0.60 mmol) were added, and the mixture was heated at 40° C. for 2 hours and at RT for 16 hours. Then triethylamine (138 μL, 1.00 mmol) and 3-methylbenzyl bromide (54 μL, 0.40 mmol) were added to the mixture, and stirring was continued for 2 hours. The reaction mixture was partitioned between water and DCM, and the aqueous layer was extracted with DCM (3×15 mL), and the organic phase was collected and concentrated. The crude was purified by silica gel flash chromatography (eluent DCM/MeOH 99:1) to yield the title compound (130 mg, 57.2% yield).

Workup

  1. customThe reaction mixture was partitioned between water and DCM
  2. extractionthe aqueous layer was extracted with DCM (3×15 mL)
  3. customthe organic phase was collected
  4. concentrationconcentrated
  5. customThe crude was purified by silica gel flash chromatography (eluent DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-c8a0c6f5b6494f429e8b6c6ae165a1a8
Source dataset
uspto-grants-2014_04
Patent number
US08710037B2

Reaction notes

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