Methanol → HCID 86644636, compound

HRID 1662077Notes

Reaction equation

HRID 1662077 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:35]([NH:37][C@H:38]1[CH2:42][CH2:41][CH2:40][C@H:39]1[C:43]([O:45][CH3:46])=[O:44])=[O:36])[NH:16][C:17](=[O:34])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][O:27]C2CCCCO2)[CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:35]([NH:37][C@H:38]1[CH2:42][CH2:41][CH2:40][C@H:39]1[C:43]([O:45][CH3:46])=[O:44])=[O:36])[NH:16][C:17](=[O:34])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][OH:27])[CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 86644637HCID 86644637, compound

Product 1

HCID 86644636HCID 86644636, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl (1R,2S)-2-[(N5-[(benzyloxy)carbonyl]-N2-{3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]benzoyl}-L-ornithyl)amino]cyclopentanecarboxylate (0.64 g), methanol (10 ml), and methylene chloride (6.0 ml) was added p-toluenesulfonic acid monohydrate (0.22 g) under ice-cooling, followed by stirring at room temperature over one night. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain methyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[3-(2-hydroxyethoxy)benzoyl]-L-ornithyl}amino)cyclopentanecarboxylate (0.39 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  3. additionwas added to the residue
  4. washby washing with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5a4fc0cfc48c42af8fea3a9f4980fcfc
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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