L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 66902459, compound

HRID 2242294Notes

Reaction equation

HRID 2242294 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:20]([O:22][C:23]([C@:25]1([NH2:37])[CH2:30][C@H:29]([OH:31])[C@@H:28]2[C@H:26]1[C@H:27]2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:24])[CH3:21]>ClCCl>[CH2:20]([O:22][C:23]([C@:25]1([NH:37][C:17](=[O:19])[CH:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:30][C@H:29]([OH:31])[C@@H:28]2[C@H:26]1[C@H:27]2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:24])[CH3:21]

Participants

4

Reactant 2

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 66902392HCID 66902392, compound

Product 1

HCID 66902459HCID 66902459, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepare according to the General Procedure A using Boc-L-phenylalanine (772 mg, 2.91 mmoles) and (1S,2S,4S,5R,6R)-2-amino-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester (480 mg, 1.94 mmoles, Preparation 22). Concentrate the crude reaction mixture, dissolve in dichloromethane, flash through a short silica gel plug with ethyl acetate/DCM (1:1), and concentrate in-vacuo to give a yellow oil. Further purify the material by silica gel chromatography eluting with 30% ethyl acetate/hexanes to 80% ethyl acetate/hexanes to afford 852 mg (87%) of the title compound.

Workup

  1. customPrepare
  2. concentrationConcentrate the crude
  3. customreaction mixture
  4. concentrationflash through a short silica gel plug with ethyl acetate/DCM (1:1), and concentrate in-vacuo
  5. customto give a yellow oil
  6. customFurther purify the material by silica gel chromatography
  7. washeluting with 30% ethyl acetate/hexanes to 80% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9a080b9f7b3d4bee8968aa83626c4822
Source dataset
uspto-grants-2010_03
Patent number
US07671082B2

Reaction notes

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