Tetrahydrofuran → HCID 66745061, compound

HRID 1959460Notes

Reaction equation

HRID 1959460 reaction equation
[C:1]([O:5][C:6]([N:8]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:9]1[N:10]=[CH:11][C:12]([N:36]2[CH2:41][C@H:40]3[C@H:38]([CH:39]3[C:42]([O:44]CC)=[O:43])[CH2:37]2)=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:28])=[CH:22][CH:21]=2)=[N:18][N:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:9]1[N:10]=[CH:11][C:12]([N:36]2[CH2:41][C@H:40]3[C@H:38]([CH:39]3[C:42]([OH:44])=[O:43])[CH2:37]2)=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:28])=[CH:22][CH:21]=2)=[N:18][N:19]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66745509HCID 66745509, compound

Product 1

HCID 66745061HCID 66745061, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (1R,5S)-3-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylate (270 mg, 0.37 mmol) in of 2:1 THF: MeOH (1 mL) was added NaOH (550 μL, of 1 M, 0.55 mmol). The reaction mixture was stirred for 30 minutes at room temperature. The solvent was evaporated to obtain (1R,5S)-3-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid, which was used for the next step without further purification.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1ec6958f89364db884bc854b4f01adeb
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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