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O-Methyltyramine → HCID 36760427, compound

HRID 1876283
Notes
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Reaction equation

HRID 1876283 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[C:25]([OH:27])=O)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH3:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([CH2:34][CH2:35][NH2:36])=[CH:32][CH:31]=1.C(N(C(C)C)CC)(C)C.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[C:25](=[O:27])[NH:36][CH2:35][CH2:34][C:33]1[CH:37]=[CH:38][C:30]([O:29][CH3:28])=[CH:31][CH:32]=1)=[O:19])([CH3:14])([CH3:15])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 4657O-MethyltyramineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 36760427
HCID 36760427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18.9 g of N-(Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride are added to a cooled solution of 20.04 g of (S)-Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester, 14.9 g of 4-methoxyphenethylamine, 16.9 ml of diisopropylethylamine and 13.2 g of 1-hydroxy-benzotriazole in 250 ml of CH2Cl2. The reaction mixture obtained is stirred at rt for 16 hours, the reaction is quenched with aq. 2N HCl solution and the aq. phase obtained is extracted with CH2Cl2. The combined organic phases obtained are washed with aq. 2N HCl solution, brine and aq. saturated NaHCO3 solution, dried and solvent is evaporated. The residue obtained is purified by recrystallisation with EtOAc/hexane (1/3) to afford the title compound.

Workup

  1. customThe reaction mixture obtained
  2. customthe reaction is quenched with aq. 2N HCl solution
  3. customthe aq. phase obtained
  4. extractionis extracted with CH2Cl2
  5. customThe combined organic phases obtained
  6. washare washed with aq. 2N HCl solution, brine and aq. saturated NaHCO3 solution
  7. customdried
  8. customsolvent is evaporated
  9. customThe residue obtained
  10. customis purified by recrystallisation with EtOAc/hexane (1/3)

Sources & evidence

ORD record
ord-92ea93b2d50247039d1a5f3c6eb8b9f5
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309596B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes