Formic Acid → HCID 58392673, compound

HRID 446832Notes

Reaction equation

HRID 446832 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.[CH3:35][C:36]([CH3:41])([CH3:40])[CH2:37][CH:38]=O.C(O)=O>C(#N)C>[CH3:35][C:36]([CH3:41])([CH3:40])[CH2:37][CH2:38][N:23]1[CH2:24][C@:25]2([C:26](=[O:32])[CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:21]([CH2:20][C@H:7]3[C@H:8]4[C@@:3]([F:2])([C@:16]5([CH3:17])[C:11]([C@@H:10]([F:19])[CH2:9]4)=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]5)[C@@H:4]([OH:34])[CH2:5][C@@:6]32[CH3:33])[CH2:22]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 763353,3-DimethylbutanalHCID 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 58392673HCID 58392673, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of compound 20 (900 mg, 1.800 mmol), 3,3-dimethylbutyraldehyde (904 μl, 7.20 mmol), formic acid (552 μl, 14.40 mmol) and TEA (251 μl, 1.800 mmol) in acetonitrile (45 ml) is irradiated with microwaves (140° C., 15 minutes). The reaction is partitioned between AcOEt and NaHCO3 solution. The organic layers are then washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated to give a oil which is purified by silica gel chromatography (from DCM:MeOH 100:0 to 98.5:1.5) to give the title compound (721 mg, 1.316 mmol, 73.1% yield).

Workup

  1. customThe reaction is partitioned between AcOEt and NaHCO3 solution
  2. washThe organic layers are then washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent is evaporated
  6. customto give a oil which
  7. customis purified by silica gel chromatography (from DCM:MeOH 100:0 to 98.5:1.5)

Sources & evidence

ORD record
ord-d9b4b1f101b0416aa68b772880494043
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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