Diethylamine → HCID 66617235, compound

HRID 1437127Notes

Reaction equation

HRID 1437127 reaction equation
C[O:2][C:3](=O)[C:4]([N:13](N)[CH2:14][CH:15](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[CH2:16][O:17]C(C)(C)C)([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH3:8].C(=O)(O)[O-].[Na+].[C:46](Cl)([O:48][CH2:49][CH:50]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[C:56]2[C:51]1=[CH:52][CH:53]=[CH:54][CH:55]=2)=[O:47].C([NH:66]CC)C>C(OCC)(=O)C.O>[C:46]([N:13]1[CH2:14][CH:15]([CH2:16][OH:17])[NH:66][C:3](=[O:2])[C:4]1([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH3:8])([O:48][CH2:49][CH:50]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[C:56]2[C:51]1=[CH:52][CH:53]=[CH:54][CH:55]=2)=[O:47]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 131727779HCID 131727779, compound

Product 1

HCID 66617235HCID 66617235, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 10 mmol of compound (88) in 30 mL of 30% diethyl amine in ethyl acetate is stirred at room temperature overnight, and then concentrated to dryness. The residue is dissolved in 20 mL of tetrahydrofuran and 10 mL of water, 2.52 g (30 mmol) of solid sodium bicarbonate is added, followed by 3.36 g (13 mmol) of Fmoc-Cl. The mixture is stirred for 3 hours, diluted with 50 mL of ethyl acetate, the layers separated, and the organic layer washed with 30 mL of water, dried over magnesium sulfate, and concentrated. The crude mixture is dissolved in a solution of 10 mL of 90% trifluoroacetic acid in dichloromethane, stirred for 2 hours, and then concentrated to dryness. The residue is dissolved in ethyl acetate and washed with 50 mL of a saturated solution of sodium bicarbonate, dried over magnesium sulfate, and concentrated. Compound (89) is purified by silica gel column chromatography.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue is dissolved in 20 mL of tetrahydrofuran
  3. customthe layers separated
  4. washthe organic layer washed with 30 mL of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. dissolutionThe crude mixture is dissolved in a solution of 10 mL of 90% trifluoroacetic acid in dichloromethane
  8. stirringstirred for 2 hours
  9. concentrationconcentrated to dryness
  10. dissolutionThe residue is dissolved in ethyl acetate
  11. washwashed with 50 mL of a saturated solution of sodium bicarbonate
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated
  14. customCompound (89) is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea4abe83988040ec9afd06ba49079614
Source dataset
uspto-grants-2009_11
Patent number
US07622440B2

Reaction notes

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