Ethyl Acetate → HCID 53759858, compound

HRID 487228Notes

Reaction equation

HRID 487228 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:11]1([O:17][P:18]([CH2:27][NH:28][C@@H:29]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[CH:41][CH:40]=2)[C:30]([NH:32][CH2:33][CH2:34][C:35](O)=[O:36])=[O:31])([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.CN(CCCN=C=NCC)C.C(OCC)(=O)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[C:11]1([O:17][P:18]([CH2:27][NH:28][C@@H:29]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[CH:43][CH:44]=2)[C:30]([NH:32][CH2:33][CH2:34][C:35]([O:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[CH2:1][CH2:2][CH2:3]3)=[O:36])=[O:31])([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:19])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 151185-IndanolHCID 132812Cgs 25462HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 53759858HCID 53759858, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Indanol (52.9 mg, 0.394 mmol) is added in one portion to a solution of (S)-N-[2-(diphenylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionic acid (200 mg, 0.394 mmol) in methylene chloride (25 ml). 4-(N,N-Dimethylamino)pyridine (48.1 mg, 0.394 mmol) is added followed by N-dimethylaminopropyl-N'-ethylcarbodiimide hydrochloride (151 mg, 0.788 mmol). The solution is stirred at room temperature for 3 hours. Ethyl acetate (60 mL) and water (15 mL) are added. The organic layer is subsequently washed with a saturated solution of sodium bicarbonate (2×15 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel, eluting with ethyl acetate-hexane (1:1). Evaporation of the pure fraction yields 5-indanyl (S)-N-[2-(diphenylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate, as a thick colorless oil that can be crystallized from ether, m.p. 89°-91°.

Workup

  1. washThe organic layer is subsequently washed with a saturated solution of sodium bicarbonate (2×15 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash-chromatography on silica gel
  6. washeluting with ethyl acetate-hexane (1:1)
  7. customEvaporation of the pure fraction

Sources & evidence

ORD record
ord-9079e5ce0bf54221845acbf7f72bd725
Source dataset
uspto-grants-1994_03
Patent number
US05294632

Reaction notes

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