Hydrochloric Acid → HCID 86644629, compound

HRID 1662067Notes

Reaction equation

HRID 1662067 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:29]([NH:31][C@H:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:30])[NH:16][C:17]([C:19]1[N:20]([CH3:28])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=O)C1C=CC=CC=1.CO.[ClH:46]>[C].[Pd].C1COCC1>[ClH:46].[CH3:28][N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[C:19]1[C:17]([NH:16][C@H:15]([C:29]([NH:31][C@H:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:30])[CH2:14][CH2:13][CH2:12][NH2:11])=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86644631HCID 86644631, compound

Product 1

HCID 86644629HCID 86644629, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (3.0 g), methanol (50 ml), and THF (50 ml) were added 1 M hydrochloric acid (5.1 ml) and palladium-carbon (5.4 g) under ice-cooling, followed by stirring at room temperature for 3 hours under a hydrogen atmosphere. The insolubles of the reaction mixture were separated by filtration through Celite and the filtrate was concentrated under reduced pressure to obtain tert-butyl (1R,2S)-2-({N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate hydrochloride (2.6 g).

Workup

  1. temperaturecooling
  2. customThe insolubles of the reaction mixture were separated by filtration through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-230cbefb8a8f4123a4e957e3857accfe
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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