Fmoc-Gly-OH → 3-Phenylprop-2-en-1-amine

HRID 1957468Notes

Reaction equation

HRID 1957468 reaction equation
Cl[CH2:2][CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([NH:28]CC(O)=O)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O>>[NH2:28][CH2:2][CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 93124Fmoc-Gly-OHHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 203693-Phenylprop-2-en-1-amine

Procedure

Aminomethyl styrene resin was prepared from chloromethyl styrene resin (Polumer Laboratories, PL-CMS Resin, 1.0 meq/g) using the procedure of Weinshenker. Weinshenker, N. M.; Shen, C. M.; Wong, J. Y., Organic Synthesis, vol. 56, pp. 95-99. The aminomethyl resin was coupled with N-(Fmoc)glycine using a procedure similar to that described in Example 7. The Fmoc group was removed using a procedure similar to that described in Example 8. This sequence was repeated three times to give the title compound, which has three glycine residues attached to the polystyrene resin.

Workup

  1. custom, Organic Synthesis, vol. 56
  2. customThe Fmoc group was removed

Sources & evidence

ORD record
ord-a6342c0f17364bb08e19dd57cb7b2e2c
Source dataset
uspto-grants-1998_07
Patent number
US05786218

Reaction notes

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