Dichloromethane methanol ammonium hydroxide → N-(2-benzothiazolyl)-O-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-L-tyrosine

HRID 1759694Notes

Reaction equation

HRID 1759694 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]([C:33]([O:35]CC)=[O:34])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[CH2:29][CH2:28][CH2:27][NH:26][C:25]=3[N:24]=2)=[CH:15][CH:14]=1.C(Cl)Cl.CO.[NH4+].[OH-]>C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]([C:33]([OH:35])=[O:34])[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[CH2:29][CH2:28][CH2:27][NH:26][C:25]=3[N:24]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 86594969Ethyl N-(2-benzothiazolyl)-O-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-L-tyrosinate

Product 1

HCID 86594970N-(2-benzothiazolyl)-O-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-L-tyrosine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The operation is carried out as for 1-6 but starting with 0.15 ml of 2N soda (0.3 mmole) and 80 mg of 2-1 (0.155 mmole) in 5 ml of ethanol. Rf=0.28 (CH2Cl2/MeOH/NH4OH 90/10/1)

Sources & evidence

ORD record
ord-aafee938d93a494dba06270f9dc45e5a
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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