Lithium Hydroxide → HCID 178508764, compound

HRID 2170097Notes

Reaction equation

HRID 2170097 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-5127a831710b486d9cbadadbced59698
Source dataset
uspto-grants-2015_06
Patent number
US09050339B2

Reaction notes

Loading…