HCID 86710795, compound → HCID 86710794, compound

HRID 1400739Notes

Reaction equation

HRID 1400739 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[N:39][C:38]2=[CH:42][C:35]3=[N:36][N:37]2[C:12]=1[N:13]1[CH2:50][CH2:49][C:16]([CH3:51])([O:17][CH2:18][CH:19]=[CH:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[CH:26][C:27]([C:44]([F:47])([F:46])[F:45])=[CH:28][C:29]=2[C:30]2[CH:43]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[N:39][C:38]2=[CH:42][C:35]3=[N:36][N:37]2[C:12]=1[N:13]1[CH2:14][CH2:15][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[CH:26][C:27]([C:44]([F:46])([F:45])[F:47])=[CH:28][C:29]=2[C:30]2[CH:43]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:49][CH2:50]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86710795HCID 86710795, compound

Product 1

HCID 86710794HCID 86710794, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl (2S)-2-(tert-butoxy)-2-[(22S,24Z)-4,22,28-trimethyl-17-(trifluoromethyl)-21,27-dioxa-1,5,7,8-tetraazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetate (50 mg, 0.071 mmol), 10% Pd/C (7.53 mg, 7.07 μmol) in MeOH (2 mL) was stirred under a H2 balloon for 2 h. It was then filtered, concentrated and purified by biotage eluting with 20% EtOAc/hexane to isolate 38 mg of methyl (2S)-2-(tert-butoxy)-2-[(22S)-4,22,28-trimethyl-17-(trifluoromethyl)-21,27-dioxa-1,5,7,8-tetraazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate as an off-white solid. LCMS (M+1)=709.3.

Workup

  1. filtrationIt was then filtered
  2. concentrationconcentrated
  3. custompurified by biotage
  4. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-0cf7ffd2fc17419d850616085a2ee90e
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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