L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 69688105, compound

HRID 1872215Notes

Reaction equation

HRID 1872215 reaction equation
[CH3:1][C:2]([O:5][C:6]([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:7])([CH3:4])[CH3:3].[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][NH:21]1>>[C:2]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]([N:21]1[CH2:22][C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20]1)=[O:19])([CH3:1])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 422478Isoindoline

Product 1

HCID 69688105HCID 69688105, compound

Procedure

N-t-Boc-L-phenylalanine (1 mmol) and isoindoline (J. Org. Chem. 1988, 53, p5382, 70-80% purity, 1 mmol) were coupled according to Procedure A and the product purified by chromatography on silica gel eluted with 20% and 50% ethyl acetate-hexanes giving an amber oil (88 mg, 23%): TSPMS 367 (MH+, 100%).

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 20% and 50% ethyl acetate-hexanes giving an amber oil (88 mg, 23%)

Sources & evidence

ORD record
ord-431a25ddeedb4a2abd52bd8b2862ad0a
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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