methyl (2S)-2-(4,32-dimethyl-29-oxa-5,7,8,26-tetrazaheptacyclo[24.6.2.16,9.110,14.02,7.015,20.030,34]hexatriaconta-1(33),2,4,6(36),8,10,12,14(35),15,17,19,23,30(34),31-tetradecaen-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetate → methyl (2S)-2-(4,32-dimethyl-29-oxa-5,7,8,26-tetrazaheptacyclo[24.6.2.16,9.110,14.02,7.015,20.030,34]hexatriaconta-1(33),2,4,6(36),8,10,12,14(35),15,17,19,30(34),31-tridecaen-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetate

HRID 1400710Notes

Reaction equation

HRID 1400710 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:42]([CH3:43])=[N:41][C:40]2=[CH:44][C:37]3=[N:38][N:39]2[C:12]=1[C:13]1[CH:47]=[C:46]2[C:16]([O:17][CH2:18][CH2:19][N:20]2[CH2:21][CH:22]=[CH:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=2[C:32]2[CH:45]=[C:36]3[CH:35]=[CH:34][CH:33]=2)=[CH:15][C:14]=1[CH3:48])[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:42]([CH3:43])=[N:41][C:40]2=[CH:44][C:37]3=[N:38][N:39]2[C:12]=1[C:13]1[CH:47]=[C:46]2[C:16]([O:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=2[C:32]2[CH:45]=[C:36]3[CH:35]=[CH:34][CH:33]=2)=[CH:15][C:14]=1[CH3:48])[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86710762methyl (2S)-2-(4,32-dimethyl-29-oxa-5,7,8,26-tetrazaheptacyclo[24.6.2.16,9.110,14.02,7.015,20.030,34]hexatriaconta-1(33),2,4,6(36),8,10,12,14(35),15,17,19,23,30(34),31-tetradecaen-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetate

Product 1

HCID 86710761methyl (2S)-2-(4,32-dimethyl-29-oxa-5,7,8,26-tetrazaheptacyclo[24.6.2.16,9.110,14.02,7.015,20.030,34]hexatriaconta-1(33),2,4,6(36),8,10,12,14(35),15,17,19,30(34),31-tridecaen-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl (2S)-2-(tert-butoxy)-2-[4,32-dimethyl-29-oxa-5,7,8,26-tetraazaheptacyclo[24.6.2.16,9.110,14.02,7.015,20.030,34]hexatriaconta-1 (32),2,4,6(36),8,10(35), 11,13,15 (20),16,18,23,30,33-tetradecaen-3-yl]acetate in MeOH (4 mL), was treated with 10 wt % Pd/C (5 mg, 0.05 mmol), evacuated and hydrogen purged three times, then stirred under hydrogen atmosphere for 18 h. The reaction was filtered (0.45 μm syringe tip filter), concentrated to a film, and the residue was used immediately in the following step. LCMS (M+H)=645.4.

Workup

  1. customevacuated
  2. customhydrogen purged three times
  3. filtrationThe reaction was filtered
  4. filtration(0.45 μm syringe tip filter)
  5. concentrationconcentrated to a film

Sources & evidence

ORD record
ord-955303a095db4762a08709d2d4234a71
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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