Lithium Hydroxide → HCID 178508764, compound

HRID 386701Notes

Reaction equation

HRID 386701 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([N:19]2[CH2:40][CH2:39][C:22]3([NH:26]/[C:25](=[N:27]/[C:28]([C:30]4[C:35]([NH2:36])=[N:34][C:33]([NH2:37])=[C:32]([Cl:38])[N:31]=4)=[O:29])/[NH:24][CH2:23]3)[CH2:21][CH2:20]2)=[O:18])[CH:12]=1)=[O:9])C.[Li+].[OH-]>C1COCC1>[NH2:36][C:35]1[C:30]([C:28](/[N:27]=[C:25]2/[NH:26][C:22]3([CH2:39][CH2:40][N:19]([C:17]([C:13]4[CH:12]=[C:11]([NH:10][C:8](=[O:9])[NH:7][CH2:6][CH2:5][C:4]([OH:41])=[O:3])[CH:16]=[CH:15][CH:14]=4)=[O:18])[CH2:20][CH2:21]3)[CH2:23][NH:24]/2)=[O:29])=[N:31][C:32]([Cl:38])=[C:33]([NH2:37])[N:34]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178472112HCID 178472112, compound

Product 1

HCID 178508764HCID 178508764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[3-(3-{2-[(E)-3,5-diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-phenyl)-ureido]-propionic acid ethyl ester (step 1) (2.17 g, 3.70 mmol) in THF (20 ml) was treated with LiOH (0.167 g, 4.07 mmol) and the reaction mixture was stirred at RT for 1 h. The mixture was partitioned between EtOAc and water and the aqueous portion was acidified to neutral pH and concentrated in vacuo. The residue was suspended in water (100 ml), and the resulting suspension was filtered, washed with cold water (100 ml) and dried to afford the title product; LC-MS Rt 0.73 mins; 559.3 [M+H]+, Method 2minLC_v003.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. concentrationconcentrated in vacuo
  3. filtrationthe resulting suspension was filtered
  4. washwashed with cold water (100 ml)
  5. customdried

Sources & evidence

ORD record
ord-58197fa3517f42539e34a222e93df148
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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