Potassium Carbonate → Hydrochloric Acid

HRID 748610Notes

Reaction equation

HRID 748610 reaction equation
C(OC(NCCNCCNC(OC(C)(C)C)=O)=O)(C)(C)C.C(C1C=CC(CBr)=CC=1)#N.C([O-])([O-])=O.[K+].[K+].C(OC(NCCN(C1C=C(C)C=CC=1C#N)CCNC(OC(C)(C)C)=O)=O)(C)(C)C.[ClH:68].CCOCC.[C:74]([C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][N:78]=1)(=[O:76])C.[BH4-:83].[Na+:84]>CO.CC#N>[N:78]1[CH:79]=[CH:80][CH:81]=[CH:82][C:77]=1[CH:74]=[O:76].[BH4-:83].[Na+:84].[ClH:68]

Participants

12

Reactant 7

HCID 11430Potassium CarbonateHCID 142862-AcetylpyridineHCID 869964-(Bromomethyl)benzonitrileHCID 4311764Sodium borohydrideHCID 10953452Ether hydrochlorideHCID 15157893tert-butyl N-{2-[(2-{[(tert-butoxy)carbonyl]amino}ethyl)amino]ethyl}carbamateHCID 69032449Bis(2-tert-butoxycarbonylaminoethyl)amino-4-methylphenylcyanide

Product 3

HCID 313Hydrochloric AcidHCID 142732-PyridinecarboxaldehydeHCID 4311764Sodium borohydride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of bis(2-tert-butoxycarbonylaminoethyl)amine (0.01 mol), 4-cyanobenzyl-bromide (0.01 mol), K2CO3 (0.05 mol), and CH3CN (70 mL) was heated at 60° C. for 10 hours. The resultant bis(2-tert-butoxycarbonylaminoethyl)amino-4-methylphenylcyanide was deprotected using HCl/ether, condensed with 2-acetyl pyridine (0.01 mol) in MeOH, and then reduced by NaBH4. After sequential treatments with pyridine-2-carboxaldehyde, NaBH4, and HCl, compound 110 was obtained in 75% overall yield.

Sources & evidence

ORD record
ord-ae2070517a354cba97e0af6f6803cd24
Source dataset
uspto-grants-2008_07
Patent number
US07399776B2

Reaction notes

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