Tranylcypromine → HCID 69197387, compound

HRID 31377

Reaction equation

HRID 31377 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@@H:4]1[CH2:8][C@H:7]([C:9]([OH:11])=O)[CH2:6][N:5]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[C:46]1([CH:52]2[CH2:54][CH:53]2[NH2:55])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>O1CCOCC1.C(Cl)Cl>[CH3:1][O:2][C:3]([CH:4]1[CH2:8][CH:7]([C:9](=[O:11])[NH:55][CH:53]2[CH2:54][CH:52]2[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:6][N:5]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:22]

Participants

7

Reactant 4

HCID 5530TranylcypromineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 69197850HCID 69197850, compound

Product 1

HCID 69197387HCID 69197387, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of cis-N-(benzyloxycarbonyl)-4-carboxy-proline methyl ester (615 mg, 2 mmol) and HOSu (173 mg, 3 mmol) in 1,4-dioxane (2 mL) was added a solution of DCC (454 mg, 2.2 mmol) in CH2Cl2 (2 mL). After 10 min at room temperature, 2-phenylcyclopropylamine (266 mg, 2 mmol) in CH2Cl2 (1 mL) was added with stirring. After 16 h, the resulting N,N′-dicyclohexylurea was removed by filtration. The filtrate was washed with saturated aqueous NaHCO3 (5 mL), 1 N aqueous citric acid (5 mL), water (5 mL), dried over MgSO4 and concentrated. The residue was purified by a silica gel column using hexane/EtOAc (6:4) as eluant to yield the desired compound as a colorless oil (633 mg, 75%).

Workup

  1. waitAfter 16 h
  2. customthe resulting N,N′-dicyclohexylurea was removed by filtration
  3. washThe filtrate was washed with saturated aqueous NaHCO3 (5 mL), 1 N aqueous citric acid (5 mL), water (5 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-26527388890d4e089a4090d1d975f81f
Source dataset
uspto-grants-2008_09
Patent number
US07425633B2

Linked notes

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