HCID 53833543, compound → HCID 54269592, compound

HRID 429748Notes

Reaction equation

HRID 429748 reaction equation
C(OC([N:8]1[CH2:33][CH2:32][CH2:31][C@H:9]1[C:10]([NH:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:15])=[O:11])=O)(C)(C)C>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[NH:8]1[CH2:33][CH2:32][CH2:31][C@H:9]1[C:10]([NH:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:15])=[O:11]

Participants

4

Reactant 1

HCID 53833543HCID 53833543, compound

Product 1

HCID 54269592HCID 54269592, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A suspension of the compound (9) (1.47 g, 3.02 mmol) in trifluoroacetic acid (14 ml) was stirred for 2 h under ice-cooling. The reaction mixture was diluted with toluene and the resulting mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and sodium hydrogencarbonate aq. The organic layer was washed with water and concentrated in vacuo to give 1.08 g of tetradecyl L-prolyl-glycinate (10) as powder.

Workup

  1. temperaturecooling
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and sodium hydrogencarbonate aq. The organic layer
  4. washwas washed with water
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d19f33a7aa19475c9e888d00d9826c1e
Source dataset
uspto-grants-2001_11
Patent number
US06319902B1

Reaction notes

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