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

HRID 583267Notes

Reaction equation

HRID 583267 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-9edcbebd9f2540d1804d578566459a2c
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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