Hydrochloric Acid → HCID 68413894, compound

HRID 1662072Notes

Reaction equation

HRID 1662072 reaction equation
[CH2:1]([O:8][C:9]([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)=[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:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]([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]([OH:39])=[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:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86644634HCID 86644634, compound

Product 1

HCID 68413894HCID 68413894, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl (1S,2R)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (0.25 g), THF (2.0 ml), and methanol (2.0 ml) was added a 1 M aqueous sodium hydroxide solution (2.0 ml) under ice-cooling, followed by stirring at room temperature for 5 hours. To the reaction mixture was added 1 M hydrochloric acid (2.0 ml) under ice-cooling, followed by stirring at room temperature. The solid precipitated was collected by filtration and washed with water to obtain (1S,2R)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylic acid (0.22 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature
  4. customThe solid precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-18b54c9f714946409ee5dc58753b221e
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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