Sodium Chloride → N,N-Diethyl-2-(phenylmethoxy)carbonyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetamide

HRID 369967Notes

Reaction equation

HRID 369967 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]([N+:21]([O-:23])=[O:22])=[CH:16][CH:17]=3)[CH:12]2[CH2:24][C:25]([OH:27])=O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:60]([NH:62][CH2:63][CH3:64])[CH3:61].C(N(C(C)C)CC)(C)C.[Na+].[Cl-]>CN(C=O)C>[CH2:60]([N:62]([CH2:63][CH3:64])[C:25](=[O:27])[CH2:24][CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=2)[CH2:19][CH2:20][N:11]1[C:9]([O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:10])[CH3:61]

Participants

8

Reactant 6

HCID 5234Sodium ChlorideHCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 215843362-(Phenylmethoxy)carbonyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetic acid

Product 1

HCID 21584373N,N-Diethyl-2-(phenylmethoxy)carbonyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(phenylmethoxy)carbonyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetic acid (5.0 g, 13.5 mmols), HOBT (1.8 g, 13.5 mmols) and TBTU (4.3 g, 13.5 mmols) in DMF (50 ml) was added diethylamine (13.5 mmols). To this was added slowly diisopropylethylamine (7.0 ml) and the reaction was then stirred for 48 h. The reaction was then poured into saturated NaCl and the aqueous phase then extracted with ethyl acetate (3×100 ml). The solvent was evaporated to leave a crude oil which was used as such.

Workup

  1. extractionthe aqueous phase then extracted with ethyl acetate (3×100 ml)
  2. customThe solvent was evaporated
  3. customto leave a crude oil which

Sources & evidence

ORD record
ord-d18452e7592c4a368a13828891fa82ca
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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