N-carbobenzyloxyalanine → HCID 67788511, compound

HRID 2226384Notes

Reaction equation

HRID 2226384 reaction equation
[NH:1]1[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:15]([O:22][C:23]([NH:25][C@H:26]([C:28](O)=[O:29])[CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C>[CH2:15]([O:22][C:23]([NH:25][C@H:26]([C:28]([N:1]1[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][C@@H:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:29])[CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 736104N-carbobenzyloxyalanineHCID 13069248Ethyl octahydro-1H-indole-2-carboxylate

Product 1

HCID 67788511HCID 67788511, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10.0 g of ethyl octahydroindole-2-carboxylate (prepared in as shown in paragraph A of this example) in 400 ml of ethyl acetate add 17.0 g of N-benzyloxycarbonyl-(S)-alanine, N-hydroxysuccinimide ester. Stir the reaction mixture at room temperature for 20 hours and concentrate it in vacuo. Place the residue on a column of silica gel (3000 g, 60-200 mesh) and elute with chloroform:ethyl acetate 10:1 to give 1-[N-benzyloxycarbonyl-(S)-alanyl]octahydroindole-2(R)-carboxylic acid, ethyl ester, a colorless oil [α]D26 +22.0° (ethanol) and 1-[N-benzyloxycarbonyl-(S)alanyl]octahydroindole-2(S)-carboxylic acid, ethyl ester, a colorless oil [α]D26 -96.4° (ethanol).

Workup

  1. concentrationconcentrate it in vacuo
  2. washelute with chloroform:ethyl acetate 10:1

Sources & evidence

ORD record
ord-392c94e543504299a5aed63ffb341cef
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

Loading…