Dimethylformamide → HCID 86656617, compound

HRID 2036881Notes

Reaction equation

HRID 2036881 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:21]([OH:23])=O)[CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.C1C=CC2[N:37]([OH:38])N=NC=2C=1.[O:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]1NO>ClCCl.O.C(Cl)CCl.C(N(CC)CC)C>[O:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]1[O:38][NH:37][C:21]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:20][CH2:19]2)=[O:23]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 13168123Tetrahydropyranyl hydroxylamineHCID 58399186HCID 58399186, compound

Product 1

HCID 86656617HCID 86656617, compoundYield 96.6%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 8.7 g 2-[(benzyloxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid, 94 ml DMF, 35 ml triethylamine, 4.1 g HOBt and 17 g EDC is stirred for 30 min at ambient temperature. 3.3 g of tetrahydropyran-2-yl-hydroxylamine are added and the reaction mixture is stirred overnight. The mixture is added to a mixture of 100 ml water and 200 ml dichloromethane. The organic phase is separated, washed, dried and evaporated. The crude product is purified by silica gel flash chromatography. 11.08 g of the title compound are obtained as colorless oil.

Workup

  1. stirringthe reaction mixture is stirred overnight
  2. customThe organic phase is separated
  3. washwashed
  4. customdried
  5. customevaporated
  6. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-bb057419571a4108a392c9c8eb4ba742
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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