Methanol → Morpholine-4-carboxylic acid[1-(3-cyano-pyrrolidin-3-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide

HRID 1179185Notes

Reaction equation

HRID 1179185 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][C:13]([C:36]#[N:37])([NH:16][C:17](=[O:35])[CH:18]([NH:26][C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])[CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:12]1)=O)C1C=CC=CC=1.CO>CCO.C(Cl)Cl.[Pd]>[C:36]([C:13]1([NH:16][C:17]([CH:18]([NH:26][C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])[CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[O:35])[CH2:14][CH2:15][NH:11][CH2:12]1)#[N:37]

Participants

6

Reactant 2

HCID 887MethanolHCID 22091411HCID 22091411, compound

Product 1

HCID 22260517Morpholine-4-carboxylic acid[1-(3-cyano-pyrrolidin-3-ylcarbamoyl)-2-cyclohexyl-ethyl]-amide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-Cyano-3-{3-cyclohexyl-2-[(morpholine-4-carbonyl)-amino]-propionylamino}-pyrrolidine-1-carboxylic acid benzyl ester (0.1 g, 0.20 mmol, 1.0 equiv) was dissolved in 15 mL of absolute EtOH. 10% Pd on carbon (20 mg) was added and the mixture was stirred under 1 atm of H2 until the starting material disappeared by TLC (5% MeOH in CH2Cl2. The crude mixture was filtered on diatomaceous earth and the filtrate was concentrated. The crude material was purified by reverse-phase HPLC to give two diastereomers; MS, m/z 378=M+1.

Workup

  1. filtrationThe crude mixture was filtered on diatomaceous earth
  2. concentrationthe filtrate was concentrated
  3. customThe crude material was purified by reverse-phase HPLC
  4. customto give two diastereomers

Sources & evidence

ORD record
ord-73744814876546b5b65f2962d7d727bb
Source dataset
uspto-grants-2007_10
Patent number
US07279472B2

Reaction notes

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