HCID 136387744, compound → HCID 136387746, compound

HRID 1924386Notes

Reaction equation

HRID 1924386 reaction equation
[CH:1]([C@@H:4]1[NH:27][C:26]2[O:28][C:23](=[N:24][N:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2[CH:29]=[C:30]3[C:15](=[CH:16][CH:17]=2)[C:14]([CH:31]=[CH2:32])=[CH:13][N:12]=[C:11]3[O:10][C@H:9]2[CH2:33][N:6]([C@H:7]([C:34]([O:36][CH3:37])=[O:35])[CH2:8]2)[C:5]1=[O:38])([CH3:3])[CH3:2]>CCO.[Pd]>[CH2:31]([C:14]1[C:15]2[C:30]3=[CH:29][C:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]4[O:28][C:26]([NH:27][C@@H:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:38])[N:6]5[CH2:33][C@H:9]([O:10][C:11]3=[N:12][CH:13]=1)[CH2:8][C@H:7]5[C:34]([O:36][CH3:37])=[O:35])=[N:25][N:24]=4)=[CH:17][CH:16]=2)[CH3:32]

Participants

4

Reactant 1

HCID 136387744HCID 136387744, compound

Product 1

HCID 136387746HCID 136387746, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 9 mM solution of methyl (3R,5S,8S)-8-isopropyl-7-oxo-22-vinyl-2,27-dioxa-6,9,11,12,24-pentaazapentacyclo[16.6.2.13,6.110,13.021,25]octacosa-1(24),10,12,18,20,22,25-heptaene-5-carboxylate (from Step 1) in EtOH was added 10% Pd/C (0.1 eq) and the resulting reaction mixture was stirred at RT under H2 atmosphere for 2 h. The catalyst was filtered off through a pad of CELITE and the volatiles were removed under reduced pressure to give the title compound as a colorless oil. MS (ES+) C28H35N5O5 requires: 521. Found: 522 (M+H+).

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe catalyst was filtered off through a pad of CELITE
  3. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-b42d4aaa91b14ce49404563756c3a7cf
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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