Hydrochloric Acid → HCID 20583550, compound

HRID 411752Notes

Reaction equation

HRID 411752 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C@H:19]([C:20]([NH:22][C@H:23]([C:42]([O:44]C)=[O:43])[CH2:24][C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:41])[C:33]4[C:38]([Cl:39])=[CH:37][N:36]=[CH:35][C:34]=4[Cl:40])=[CH:27][CH:26]=3)=[O:21])[C:18]3[CH:17]=[N:16][N:15]([CH2:46][CH3:47])[C:14]=3[CH2:13]2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.O[Li].O.Cl>CO.O>[Cl:8][C:6]1[CH:5]=[C:4]([S:9]([N:12]2[C@H:19]([C:20]([NH:22][C@H:23]([C:42]([OH:44])=[O:43])[CH2:24][C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:41])[C:33]4[C:38]([Cl:39])=[CH:37][N:36]=[CH:35][C:34]=4[Cl:40])=[CH:27][CH:26]=3)=[O:21])[C:18]3[CH:17]=[N:16][N:15]([CH2:46][CH3:47])[C:14]=3[CH2:13]2)(=[O:11])=[O:10])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 131723878HCID 131723878, compound

Product 1

HCID 20583550HCID 20583550, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 47 mg (0.063 mmol) of N-[(5-(3,5 -dichlorobenzensulfonyl)-1-ethyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-4 (S)-carbonyl]-4-(3′,5′-dichloroisonicotinoyl)amino-(L)-phenylalanine, methyl ester in 2 mL of MeOH and 0.5 mL of water was treated with 7 mg (0.167 mmol) of LiOH—H2O. After stirring for 2 hr the solution was acidified (pH 2) with 1.2 N HCl and concentrated in vacuo. The residue purified by preparative TLC on silica eluted with 94.5:5:0.5 CH2Cl2:MeOH:HOAc to yield N-[(5-(3,5-dichlorobenzensulfonyl)-1 -ethyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-4(S)-carbonyl]-4-(3′,5′-dichloroisonicotinoyl)amino-(L)-phenylalanine (35 mg) as a solid. LC-MS: m/e 727 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue purified by preparative TLC on silica
  3. washeluted with 94.5:5:0.5 CH2Cl2

Sources & evidence

ORD record
ord-9901704429764223b5c76d72765ae2b1
Source dataset
uspto-grants-2003_05
Patent number
US06559174B2

Reaction notes

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